Zach Selwyn

Actor. Musician. Host. Writer. Dinner Guest.

  • In the late 90’s I was lucky enough to sleep with a Playboy
    Centerfold. For the sake of this story, let’s call her “Miss July.” She
    wasn’t the current centerfold by any means, in fact her issue had
    already been off the racks for nearly seven years at the time of our
    tryst, but she had been a popular Playmate in the 90’s… and one that I
    had admired for years. For some reason, the planets aligned and she
    and I shared a three-night fling at our respected apartments doing all
    we could to pretend that we had anything in common outside of our bed
    sheets.

    Following our little hook up, I rifled through a used bookstore for
    her back issue, buying at least six copies to give to my high school
    friends. I called nearly every guy I knew to share in my glory and
    walked on air for a good three months after our encounter, knowing
    that I had achieved one of the ultimate male fantasies. I even sent a
    back issue to my dad. After all, Playboy was my bible growing up and
    bedding one of the world’s most beautiful women suddenly made me feel
    like I could accomplish anything in my life.
    Last week, while walking through a grocery store with my 10-year-old
    son, I ran into Miss July in the produce section. At first, I stopped
    and stared at her, like every man in the store had been doing since
    she walked in the vicinity. She was still gorgeous and shapely and
    wearing an outfit that only a Playmate can get away with.
    Her breasts were still high and on display. He hair still blonde and
    bountiful, with ringlets cascading beneath her shoulders – as if she
    was currently in the middle of a photo shoot. I ogled for a minute,
    before coming to the realization that she was, indeed, Miss July. My
    Miss July. The girl I had slept with all those years ago. I hadn’t
    thought of her in so long, I assumed she had moved to the other side
    of the country where I would never see her again.

    And now here she was fondling a pair of avocados.

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    “Why are you staring at that girl?” My son asked, snapping me out of
    the coma my 40-year-old mind had drifted into.

    “Oh, I think I know her,” I said, secretly hoping that he might
    recognize her beauty and high-five me after we left the grocery store.

    “Cool,” he responded. “Can I play on your phone?”

    I gathered my thoughts and strolled around to the coffee aisle. I
    wasn’t sure if I was going to say hello to her, afraid that she would
    think I was some stalker from her Playmate days. I also didn’t want
    her to blurt out something stupid, like “Oh my GOD! You were that guy
    I slept with in the 90’s!” Worst of all, I thought, she wouldn’t
    remember me at all. I let my son pick out some cereal as I mulled over
    my next move.

    Like most happily married men, I still harbor the memories of my
    single years when one-night stands were so daring and fun and
    whimsical. After all these years, they hold a nostalgic place in my
    heart as something fantastic and perfect – when in reality they were
    normally panic-riddled and led to health concerns and loneliness.
    My week with Miss July began at a nightclub in Hollywood. She was
    gorgeous, fending off the masses with her icy stare and constantly
    turning down drinks from potential suitors clamoring to be in her
    airspace. I had no idea she was a Playmate at the time, but she
    certainly had the look. She was dressed to the nines in a fur jacket
    and sipping on a vodka drink when my friends dared me to go speak to
    her. As I was in my cups, I waltzed directly up to her and began
    rubbing her jacket.

    “Interesting. A New Zealand back country field rabbit coat… Very
    rare,” I said.

    She laughed and stared me deep in the eyes.

    “Are you on ecstasy?”  She replied.

    “No,” I exclaimed. “Not at all… why?

    “Normally when I wear this coat out a bunch of druggies just want to pet it.”

    I laughed and thought of a quick comeback.

    “I’d rather pet you,” I blurted out confidently.

    She actually laughed and wrote her number down on a bar napkin. I told
    her I’d call her and I did – the next day – breaking any rules which I
    had learned from popular movies like Swingers. She was surprised to
    hear from me. We made plans to go out to a Casa Vega, a Mexican
    restaurant in the valley for margaritas the following night. When she
    cancelled on me two hours beforehand, I thought I was doomed. When I
    asked her why she had to cancel, however, my eyes lit up.

    “I have to fly to Iowa for a Playboy convention in the morning, I’m so
    sorry,” she said.

    “Why? Do you sell advertising for them or something?” I inquired.

    “No, silly – I was Miss July a few years ago! I thought you knew…”

    I didn’t know. Now I did. I immediately called my friends and sang
    them J. Giels Band lyrics through the receiver. Yes. My baby was a
    centerfold.

    Playboy Playmates

    A week later, we hit Casa Vega. At one point she went outside
    to smoke and I let her go alone. (I was trying to quit at the time).
    When a guy at the bar saw this, he motioned to me and said, “Dude, you don’t let a girl that hot out of your sight for any amount of time.”

    I ignored him, assuming she would brush off any potential creeps and
    return back to our bar stool where we’d finish our drinks and continue
    our evening. After 20 minutes, however, I began to grow nervous.
    I went out to the smoking section, and sure enough, there they were:
    MEN. All kinds… Guys who had intended to come inside for dinner but
    were so mesmerized by her beauty that they decided to hang outside a
    little longer. Guys who didn’t even smoke were bumming cigarettes from
    her and chain smoking. One guy even flipped her a business card and
    said, “I scout for Playboy, if you ever want to be in the magazine,
    let me know…”

    She laughed and to my surprise grabbed me by the arm. All the men’s
    faces dropped as they saw this 23-year-old kid with a Strokes haircut
    coyly slip his hand around the top of her waist. Dejected, the guys
    all walked inside with their heads down, preparing to settle for
    baskets of chips and salsa and not the ravishing creature who I was
    lucky enough to be spending the night with.

    We went to another bar and then went to my place. Two nights later, I
    joined her at her place. We went out once more, on a Saturday, but she
    got swept up in a crowd of famous actors and I stood around waiting
    for her to return to me, feeling like the unpopular kid in junior high
    who can’t muster up the balls to ask a girl to dance. Eventually, when
    she began partaking in their bottle service vodka, I grew frustrated,
    knowing my time was up. Without even saying good-bye, I grabbed my
    jacket and made a quick exit, calling my buddies to meet me for a
    heartbreak beer at Coach and Horses, my old favorite dive bar.

    “So what if it’s over?” My buddy said. “You were with a Playmate!”

    “Yeah dude, my last hook up was with the hostess at Yankee Doodles in
    Agoura Hills,” said another.

    As the drinks flowed, my confidence returned and I quickly got over
    the fling with the help of some good friends. The next day Miss July
    and I exchanged a few phone messages, but never reconnected.
    Even though it was over, I was still waking on air, feeling as if I
    had done all I could and was now exuding an air of confidence that
    nobody could touch. I even kept two of her back issues for myself. One
    to put on the coffee table, and one to put in a pristine cellophane
    folder where it would remain intact on my bookshelf until the end of
    my days… It still sits there today.

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    As I rounded the bread aisle, I saw her again. As luck would have it,
    we were approaching the check out line at the same time, inspecting our carts and reaching into our wallets for ATM cards. I purposefully took the spot in line directly behind her and noticed as she unloaded
    an unusual amount of dog food onto the conveyor belt. She also bought butter, apples, avocados, bananas, Kombucha and a pre-made tray of
    sushi. I was still staring. My 10-year-old took advantage of my distant
    gaze and slipped two packs of M & M’s into my cart. I didn’t care. I
    had butterflies in my stomach as if I was back in that Hollywood
    nightclub 17 years earlier… But then it hit me: I was married. I was
    standing with my child. I had no reason to not say something. If
    anything, I thought, it would extend the memory a few more years. I
    decided to go in for the kill.

    “Is your name Taylor? (Not her real name)” I asked.

    She looked up at me and smiled.

    “Yeah, who are you?”

    “My name is Zach,” I said. “Not sure if you remember me, but we sort
    of dated about 17 years ago… we met at a nightclub and went to Casa
    Vega…?”

    She looked me over, perplexed.

    “Were you that drummer?” She asked.

    “No, but I play music…”

    “Oh, you were the guy who knew Green Day!”

    “No,” I said.

    “Oh. Did you know Quentin?”

    “Nope,” I responded, realizing that I was barely a flicker of memory
    in her mind all these years later – whereas she had held the top spot
    in my gallery of former flames for close to two decades. I was a bit
    embarrassed.

    “Oh, wait!” She said. “Did you used to have long curly hair? And you
    lived on Harper Avenue and you played me Crash into Me by Dave
    Matthews Band on your guitar?”

    The cashier chuckled.

    “Uhh, yeah, that was me,” I said, blushing.

    26288a71d9878f6519c7ca018a8dca5d-36296
    23-years-old with a Strokes haircut…

    She hugged me as if we were long lost siblings. I felt my wobbly arms
    go around her body once more, immediately wondering what would have
    happened if I hadn’t been so stubborn at that bar all those years ago.

    My chest pressed against hers and for a brief moment I was 23 again,
    stupidly running around Hollywood with a group of horny friends
    worrying about nothing but a 10 a.m. commercial audition and where I
    was going to be drinking that night. She pulled away and paid for her
    groceries and stood behind the bag boy waiting for me to pay and
    rejoin her. When I did, we caught up briefly and I introduced her to
    my son… who seemed to not have any interest in this beautiful woman
    that his dad was talking to.

    As it turns out, Miss July still did Playmate conventions. She was
    living in the valley, had been married for a year but was divorced and
    was raising her 3 small dogs, Gucci, Dorito and Mr. Farts-A-Lot. She
    didn’t go out anymore, was disappointed with Tinder and loved
    The Big Bang Theory. I felt like she was reciting her “Turn-On” list
    from her Centerfold interview page – but had updated it as a
    middle-aged woman.

    We exchanged numbers and she remarked on how handsome my son was. I
    told her I’d invite her out to see my band if we ever played again and
    I watched her speed off in her Prius. I thought back to the nights we
    had shared together and then looked back at my son, blissfully playing
    on my phone, seemingly unaware of what had transpired between his father and
    that mysterious girl in the produce section 17 years earlier.

    As we drove home, he handed me back my phone and stared out the
    window. As I watched his eyes dart around the city, I thought of his
    future and how he was still so young and innocent and had the entire
    world ahead of him. I realized how happy I was to be spending my life
    with my wife, my daughter and him, and not a smelly pug named Mr.
    Farts-a-Lot.

    And then, after a few minutes of driving, he broke the silence.

    “Dad, I wanna learn some Dave Matthews Band songs on guitar,” he said.

    They grow up so fast…

    READ ZACH’S NERDIST STORY “RE-EXAMINING THE NBA DRAFT ID I HAD BEEN SELECTED!”

    https://nerdist.com/re-examining-the-1997-nba-draft-if-i-had-been-selected/

    CVH4QMaI

     

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  • Singer-Songwriter Zachariah Selwyn will release his 5th official LP next week, a country-hip hop concept album entitled “Firing Squad.” The record is based on an unreleased scripted western project that Selwyn has been developing for more than a year.

    “I guess I wanted to get the music out before the project was done,” Selwyn says. “I know that projects like this sometimes get sidetracked.”

    The “Firing Squad” soundtrack features female vocalist Gia Ciambotti (Bruce Springsteen/Joe Walsh) in a starring role, marking the first time the band has used utilized a second lead singer on record.

    “Gia is an absolute mesmerizing presence on a microphone,” Selwyn explains. “I keep hoping she joins our band permanently, but the road isn’t that appealing for most of us anymore so for now we’ll keep it in the studio.”

    “Firing Squad” also features longstanding band members Dan Wistrom, Bobby Joyner and producer/multi-instrumentalist Jesse Siebenberg. (Lukas Nelson).

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  • Zach Selwyn stars as DWIGHT STRIPES, a filthy, sleeves hating guitar playing Shitrocker in Bubbles’ new outlaw country band, “Bubbles and the Shitrockers!” Zach also wrote five of the songs on the soundtrack! Find out where this film is showing and get right out of ‘er and see it! Also starring Billy Bob Thornton, Ronnie Wood and your favorite Trailer Park Boys…! Dir. by Charlie Lightening

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  • BETWEEN ZEVON AND LEVON

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  • Screen Shot 2019-08-26 at 9.30.31 AM
    It was around 2:15 in the morning when a hammered single mom of three kids with a very visible C-section scar approached me following my music gig at a place called Peri’s in Marin County, California.
    “Hiiii Mr. Talented…” She slurred. “I live two blocks away and my kids are prolly asleep – D-ya wanna come have a drink and smoke and hang ouuuuut?”
    I looked this woman over. She was about 40, had a swollen and (possibly) fractured purple ankle and was heavily puffing on an e-cigarette…. From behind, half of her dress had hiked up and lodged itself in her butt, revealing a horrifying leg tattoo of a dragonfly that started mid-thigh and ended probably just above her Va-jayjay.
    She also had one dreadlock.
    “Uhhh… Well, the thing is…” I stumbled. “I’m married – sooo I don’t think it would be a good idea, ya know?”
    “Fuck you! You’re an asshole for leading me on!” she snapped.
    Wait, what? Leading her on? How was I leading her on?
    A few seconds later, it hit me… When I was performing on stage a few minutes earlier, I recalled saying:
    “Who’s the hottie in the back/Nice body, nice rack/
    Meet me outside in five – My name is Zach.” 
    Oops.
    Look. If you have ever seen me or my band perform live, I often jokingly flirt with girls in the crowd with improvisational freestyle rap lyrics from the stage… This, however, was one of those rare moments when the girl actually stuck around and thought I was serious… I felt terrible. (Here’s a sample of a freestyle from NYC in 2017)

     

    “Sorry, it was a joke, – like a part of the show??!??!?” I tried to explain to her.
    She threw a drink at me, turned around and stopped at the door to say good-bye.
    “Your music fucking sucks anyway,” she screamed.
    By the way? I never made it home that night. Since I was too drunk to drive, the bartender let me sleep in the back seat of my Prius in the bar’s parking lot…
    Did I mention it was a Tuesday?
    What the fuck am I doing?
    I am 44-years-old. I have two kids and a wife. Most men my age are in bed by 8:30 every night, binge-watching Netflix and thinking about some meeting they have at work the next day with Nancy from H.R.
    Not many dudes I know are living like me this summer… touring bars in their mid-40’s trying to sell 20-something kids t-shirts and CD’s of their country hip-hop band that – in most people’s eyes – peaked when they opened for Jason Mraz in 2008…
    For the record? On this tour I sold ZERO CD’s.
    But let’s go back a few years…
    In the 2000’s, every bar I played in was always PACKED. Friends, fans and industry folks lined up outside awaiting new songs – or a 10-minute freestyle rap where I might drop their names into a verse… They bought CD’s and shirts and sang along and I would walk out of the bar with $400 and a thousand business cards… My band played across the country and stayed in fine hotels, sipping top shelf whiskey and partying with rock stars…
    But, then came adulthood. People had kids and a lot of my musician friends got real jobs. Some band members moved out of town… Most guys gave up or got into real estate. Even I took a break from it for a while to be around the family and work in the TV business. However, the thrill of performing live was always missing…
    So, this past summer I decided that a 9-venue mini music tour of Northern California would be the best thing for my mind, body and soul.

    Railroad Station Poster jpg
    Tour posters from the road...
    Tour posters from the road…
    Guitar Heroes Flyer
    Screen Shot 2019-06-25 at 1.46.47 PM

    As the days rolled on, I sort of forgot about the ways of the road… Late nights, uncomfortable beds… bad habits reintroducing themselves… When you’re out driving down I-5 at 9:30 at night – a restaurant like Subway suddenly becomes a solid option. The Yellow American Spirit cigarette suddenly becomes “healthy” decision… Not to mention that most bars where I play like to avoid paying musicians – and instead – offer up FREE DRINKS instead – which ultimately leads to me drinking $4.99 mini bottles of Sutter Home Cabernet – guaranteeing a foggy and painful morning.
    Oh, and most bartenders who hear me ask for “the best red wine in the bar” often think I’m joking and laugh in my face.
    In all honesty, I quit drinking hard liquor ten years ago…. Waking up in a Super 8 Motel with two lines shaved into your eyebrows like D’Angelo Russell will do that to anybody… 
    But that’s a whole ‘nother story…
    The “Zachariah: Backyard and Wineries” tour began in San Francisco, at a private party where some tech geniuses of the world dug my music and my improv songs about how expensive the city had become… The host had somehow procured 25-plus bottles of the legendary Pliny the Elder beer from Santa Rosa and he was extremely generous with his liquor cabinet. However, as people got more sloshed, a supremely drunk friend of theirs named Kelly demanded I sing Shallow by Bradley Cooper and Lady Gaga.
    “Are you gonna sing it with me?” I asked her.
    “Fuck YESSS!” She screamed as the party encouraged her.
    A few chords later and she was warbling through the “Wooooaaaah – ohhh – h ohhh ohh ohh oh AWWOWOHHHWHWHWH” section of the song. Let’s just say she didn’t nail it, but it didn’t matter. The vibe and energy was fantastic and I assumed every gig would end up this beautiful and natural.
    But the next night I drove up to gig at Peri’s Bar in Marin County. It was certainly a success, but I was definitely under-paid and over-served awful tiny bottles of Sutter Home… (Thus the reason why I slept in a parking lot).
    When I woke up in the back seat of my 2008 Prius at six the next morning, having sweat through my clothes on stage the night before, I decided that a shower was indeed in order. I quickly Googled “YMCA Marin County” on my phone and found one 10 miles away where my Hollywood “Family Membership” would let me use their facilities. This is also a practice that HOMELESS people participate in.
    I ended up spending 45 minutes in the sauna listening to two men talk about their new tech venture that would “change the dumpling game forever.” After they noticed me listening in, they began whispering and eventually left the sauna altogether, protecting their billion dollar dumpling idea.
    A billion dollar dumpling idea? What I derived from this moment was that I am definitely in the wrong business…
    That night, I performed at the Lagunitas Tap Room in Petaluma. The venue was amazing and they even offered up cash ($80) for the gig. Plus, per usual, they served me all the beer I could drink. Initially I had planned on having one or two beers because I had to drive to meet my wife and kids up north in Cloverdale once the night ended…
    However, after my show, I quickly found myself 8 beers in. Since my head was spinning, I asked my new friend Pete (who booked me there) if he had a better idea than drunk driving to Cloverdale.
    “Yeah brother… my buddy Andy has an Airstream in a forest that he rents out – it’s $45 for the night,” he said.
    “Uhh… like, HOW in a forest?” I inquired.
    “It’s desolate, man… super chill and quiet and you won’t hear anybody’s voice for like, 9 hours straight!” Pete replied.
    OK. Look. I enjoy nature. I love converted Airstream trailers. But 9 hours alone in one in nature? Yo, I’m not trying to live that Into the Wild life… I am a social person. I need conversation. Shit, I need some WiFi, ya know?
    “I don’t know Pete,” I explained. “I sorta need a bed – I slept in my car last night.”
    “They have a killer Aerobed,” Pete said. “I’ve slept there sooo many times, you’ll love it – I’ll even drop you off!”

     

    And with that, Pete took me to a beautiful house with 40 acres of land in the woods, where we knocked on the door and met Pete’s buddy Andy who was extremely tired and reluctantly thrust the trailer keys into my hand. He also passed me a Romancing the Stone-like treasure map explaining how to find the forest Airstream… Pete left and I slugged through the dark forest, absolutely fearing for every second of my life, before coming across what was a beautiful 1950-something converted Airstream “Cabin.”

     

    Screen Shot 2019-08-26 at 9.13.15 AM
    This was terrifying.

    I unlocked the door and went inside. It was about as rustic as you could expect.
    There was an Aerobed with a blanket on it…
    On the wall hung a calendar from the year 2013…
    And there was a shovel in the corner next to a roll of toilet paper beneath a sign that said, “Use Nature’s Facilities.”
    Holy shit. What? So no bathroom? Was I gonna have to re-learn the “One-armed tree hang” I had been taught at summer camp as a kid?
    I decided to just crash and wake up as early as possible to split.
    30 minutes after I went to sleep, I woke up on the floor. The Aerobed had deflated. It was about 45 degrees in the trailer. With no visible air pump nearby, I turned the deflated Aerobed into a pillow and did my best to sleep for the next six hours.
    A couple of hours later I woke up to the sound of what must have been two bears humping in the woods… I also swear a mysterious light flashed across the sky and for two hours I panicked about being abducted by aliens and anally probed above the Redwoods. Eventually, around 6:30, I awoke with a stiff neck and took a $20 taxi back to my car at Lagunitas.
    Up in Cloverdale I met my family and began thinking that perhaps, the road life was no longer for me… I took the family to the local trampoline park and hit up some small town burger place and I was amazed at how comfortable the safe and respectable family life felt again… For a minute, I almost cancelled my final three gigs…
    But, since I can rarely turn down a chance to perform, I decided to carry through on my commitments.
    As I was playing the night at an all ages restaurant, the local town drunk “Banjo Bob” (yes, his real name) taught my 13-year-old son how to best hold a pool cue if he was ever to get into a bar fight.
    (His advice? Hit the guy with the skinny end, that way if it breaks off – you’re left with the more dangerous thick end of the stick as a weapon.)
    To quote my late grandmother: “That’s wonderful?”
    The following night, I played at a pretty cool bar in Healdsburg where I ate pizza that a guy had made from an oven that he dragged behind his bicycle… I know what you’re thinking: Bike Pizza? Trust me – It was absolutely delicious.
    On the last night, we drove down to San Francisco and the tour ended at a bar in the Marina called Jaxson for a friend’s fundraiser party in the city – where, as I was playing live, a man and woman dry-humped each other on the dance floor in front of me…
    Now look, I’m all for dancing, but this was kind of ridiculous… I actually didn’t care. They were wasted and they loved my music and I felt at home for a few minutes with the young Marina area crowd of San Francisco…
    Here – watch the video and make your own assumptions:

    For the record? That girl dancing did not ask me to come back to her place after the gig.
    But the guy did…
    “Hi Mr. Talented,” He said… “Wanna come party with me at my place?”
    “I’d love to, but, the thing is… I’m married,” I said.
    I woke up the next morning in the back seat of my Prius…
    ZACH IS NOW BOOKING VENUES FOR HIS SUMMER 2020 TOUR!! 

    RfW_06.1
    Red Fuckin Wine – New single coming SOON!

    www.ZachSelwyn.com
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  • https://allnashvilleroadshow.com


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Tag: Power 106

Read Zach’s New Short Story: “The Freestyle”

  • September 12, 2012
  • by zachselwyn
  • · The Writer · Uncategorized

THE FREESTYLE by ZACH SELWYN

A week ago, I got into a freestyle rap battle.

Now, I know this is not something that a 37-year-old father of two should ever be writing, but for some reason, last Wednesday night – I felt a burning desire to join an intimidating rap circle and try and drop some dope-ass, quick-minded, funny lyrics on some totally unsuspecting strangers.

If there is ever a moment in my life I could have back, it is this one.

Standing out in front of the Smokehouse restaurant in Burbank – in front of my wife and another couple – whose kid is in the same kindergarten class with our son, I decided to stumble over into a “cypher,” or crew of people rapping together in a cyclical pattern. I suddenly turned from “the bearded weirdo who always drives the soccer practice carpool,” into “the drunk dad from the kindergarten class who thought he was Eminem.”

Let me back up here a minute. See, I used to be a rapper. That is not a typo. I didn’t “wrap” presents… I RAPPED. I recorded a few CD’s and everything. I had skills. A future. A following.

I know, laugh it up…my outside appearance is deceiving. I am white, fatherly and pasty. I wear basketball shorts and t-shirts 90 percent of the time for “comfort.” I occasionally have non-dissolved Rogaine foam in my hair. I am not intimidating at all.

But, believe it or not, at one point in my younger life I was a bona-fide, authentic, legitimate, validated, record deal – having, somewhat admired freestyle rapper. Arguably, one of the best in the world. I could rhyme like Dr. Seuss on a mushroom trip. I could think off the top of my head faster than 99 percent of all improvisational actors I have encountered. I used to perform my skills live with  bands in nightclubs, at late night parties and at sketch comedy shows. I garnered mad respect. People would come up nightly and ask me, “How the hell does your mind think like that?” The truth is? I had no idea.

I bet you’re wondering how this all started…

In 1987, if you had asked my mother what career she thought I’d pursue as a young man – based on the thousands of dollars I made mastering Jose Canseco and Mark McGwire’s signatures – she most likely would have said “professional autograph forger.” (A quick arrest at the local baseball card shop in 1989 ended that career…)

She might have guessed I could have followed my father – who is a doctor – into medicine – but a quick “D” in chemistry my sophomore year of high school stifled that dream. (I even cheated. And I still got a D…)

I may have even been able to make a living in the courtroom, brandishing my gift of gab in front of honorable judges while trying to convince the jury that the defendant was not even in the country when the crime occurred… But to me, law school was for the geeks who couldn’t talk to girls at junior high parties. Or make them laugh at summer camp… Or freestyle rap their way into their pants.

“Yo Melissa/ I wanna kiss ya/Take off your dress and I wont dismiss ya…”

The first time I made a rhyme up about a girl was in eighth grade. Her name was Melissa, and we were at Dana Restival’s Halloween party. Everybody knew I was the best rapper in school – and when I dropped those lyrics to her in front of a crowd of people, she continued to follow me around the party for the rest of the night. Around 9:30, we snuck away, near a saguaro cactus in the Tucson desert – and shared our first kiss. It was sloppy, but unbelievably perfect. Brilliant and everything I had ever imagined. In my mind, Melissa was going to be my girlfriend. I thought I had it made… Problem was, she ended up letting John Coates – school hesher – feel her up on the school bus a week later.

Back in the 1980’s, if you were into rap music, it made you unique. I had a partner in crime named “Ryan the Rhymer” (Now a dentist in Tucson) – and we comprised the tightest white-boy rapping outfit at Townsend Junior High School in 1989. We were a two-man wrecking crew known as “SO FRESH.” I wore African leather medallions to school and sported those 3rd Bass/ Dwayne Wayne flip-up glasses as a way to seem more “intelligent.” We wrote raps and performed onstage as a crew at talent shows, and were basically laughed at for not listening to cheesy hair-cock rock like Poison and Slaughter. Back then, we were the musical outcasts, because we liked Beastie Boys, Shinehead and Boogie Down Productions. Then, one day, we won a student council election based on one of our raps (Called “Do it for the School!!!”) – After that, we were no longer considered out-of-touch losers.

The author, posing hard as a member of “So Fresh” in 1989. Note the chin-up bar in the doorway.

The first rap I performed at my high school was when a kid named Eric Tiberon challenged me to a rhyme-off in ninth grade. He was black, and had the entire school behind him mainly for the sole reason that he had a high-top fade that looked like Kid from “Kid ‘N Play.” When I accepted his challenge, people were somewhat scared for me… but the final parking lot battle went a little differently. Eric basically recited Eazy-E’s classic Eazy-Duz-It. I made up a rap about how much being in ninth grade sucked.

Eric rapped about his cars and his girls (Both of which he did not have).

I rapped about being beat up by a high school bully named Jason and getting a C in Geometry. I remember my verse well.

“School sucks, I get up so early/ Bully named Jason always looking so burly/ Said I looked like a freshman girlie/ stuck my head in a toilet and gave me a swirlie…”

Yeah, I know it was WILL SMITH-ish… It wasn’t hardcore or gangsta – but it was funny – and the people loved it. So much so, that Eric and I became friends after that – even going to see Ghostbusters 2 together just to hear Bobby Brown’s new song “On Our Own.” (Still holds up today. CLASSIC jam).

After that, high school was certainly an awkward stumble through athletics, music, girls and experimentation – but hip-hop music was always a staple in my life. I rapped over Humpty Dance break beats at high school proms and earned my juice on the dance floor busting out the Running Man, Roger Rabbit and the Butterfly to songs like The Choice is Yours by Black Sheep during my junior prom. By my senior year, I thought I’d even try to make a legitimate rap album.

And then The Chronic came out.

Dr. Dre’s album changed my life Suddenly, dancing wasn’t cool anymore. My style of rap sucked and whatever street cred I had amongst my Tucson, Arizona brethren went out the window. I was Vanilla Iced-out. Squashed. 187-d. Ignored.

At the time, I was surprised at how little I cared. In fact, it was a relief to know that my rap career had ended…  And the following fall I enrolled in college at USC in Los Angeles – where I engulfed myself in West Coast G-funk – but also expanded my mind into other areas of music as well. I picked up the acoustic guitar as a means to get laid – and even started my first band with my pal Jason Richards. (The only other freshman that could play more than 3 chords) We were called, sadly – “Two College Freshman.”

One-Half of “Two College Freshman” – Summer 1994. Realizing that singing Jackson Browne songs got the author laid more than trying to be a member of A Tribe Called Quest.

We were at USC – which is a terrific campus in the middle of south central Los Angeles – and we were one year removed from the famed LA riots of 1992 – so the West Coast dominance of rap music was everywhere – but I no longer wanted to be a rapper. In fact, based on the amount of girls I got when I rapped compared to how may I got when I did an acoustic guitar cover of “Your Bright Baby Blues,” I suddenly realized that I really   wanted to be JACKSON BROWNE. Especially when legends like 2Pac and Notorious BIG were murdered, I knew the rap game wasn’t exactly cut out for a 3.8 GPS-having son of a Jewish doctor.

I ended up paying tuition and making ends meet in college by DJ-ing and Emcee-ing fraternity parties and weddings – and I eventually branched out into Bar Mitzvahs after school (An entirely different story altogether). But by the time the late 90’s rolled around – and I found myself hanging around musical friends like the bands Matchbox 20, Paperback and even boy-band acquaintances like ‘NSYNC – I noticed that everybody always talked about the newest rap music out at the time. Puff Daddy, Mase, Nelly – you name it. This was the music of the time, and even the biggest musical stars I knew were obsessed with the genre. I’m not sure where it happened for the first time, but I was around some guy who began freestyle rapping. He was decent, but his trite choice of lyrics and lack of originality made me consider attempting my own rap. I jumped in. He nodded along, probably unimpressed – but nonetheless enjoying my effort. When I was done, he gave me a fist bump and walked away.

I did it again with the guys from ‘NSYNC. Living in Los Angeles in 1998 meant I had a lot of young friends who were trying to act, sing, dance, direct, produce – you name it. One of my buddies had grown up with Chris Kirkpatrick – probably best remembered as the guy Eminem threatened to beat up in a song in 2000 – and the dread-locked “bad boy” of ‘NSYNC – the most popular boy band in the history of the world. Chris and I would get drunk together and end up in some random hotel room with a bunch of girls and background dancers and rap producers at two in the morning. Somehow, after 30 Heineken bottles littered the floor and a few joints were passed, people began rapping. I started stepping in. I started getting the laughs. Making up rhymes – and ultimately having the tightest flows of any so-called “rapper” hanging around these after-parties.

Sadly, after partying with ‘NSYNC the night before on New Years Eve, the Author was comped at their concert in Las Vegas on January 1, 1999.
The most embarrassing ticket in his collection.

Once, around 1999 – I ended up in the Standard Hotel with Dr. Dre. He was surrounded by 300-pound bodyguards and a crew of slinky women who looked like they were in En Vogue. – He employed a personal “blunt-roller” and was encircled by about ten wanna-be rappers. That night was the first time I was actually afraid to rap in front of somebody in nearly ten years. In fact, after witnessing three saggy-pantsed douche-nozzles try to rap Dre’s ear off, I decided that perhaps my rap future was a pointless joke. I guess I always knew what I did in hotel rooms with my friends was more of a party-trick, and less of a career choice, and it didn’t bother me. I had no interest in becoming a professional rapper. I was committed to having fun and getting laid and occasionally jumping on-stage after 10 drinks to freestyle along with my friend’s band at their Hollywood club gigs. None of it made any sense. We were 25-years-old, wasted and happy and sleeping until noon. We were young, dumb, naïve and convinced that fame and success was just around the corner. One of my friends, a former hip-hop dancer for the local rap station Power 106 – began calling me “Zachariah.” I immediately took on the moniker as my rap handle. “Zachariah, the Rhyme Messiah.” There it was. My party trick. I would go around any room and rap about what people were doing, wearing, drinking, you name it. I never thought it would lead to anything but a few free drinks and some laughter.

And then somebody offered me a record deal.

The first studio time I ever had booked was around this time. A girl I had fooled around with named Lisa knew a rap producer named “Cookie” and she arranged a meeting for us at the Skybar on Sunset Boulevard. I wasn’t sure what I was going to do during this meeting, but I put on a cowboy shirt and fluffed my hair up to Lindsay Buckingham –heights. Anything to seem somewhat marketable and charismatic.

At the time, nobody in LA had any type of haircut but a short spiked boy-band thing, so my wild Jew-fro gave me a little edge. It somehow made me a bit more reckless. Maybe even dangerous  – if only in that “I don’t give a fuck” drug-addict look that you see outside of Venice Beach grocery stores.

At the Skybar, “Cookie” – as he introduced himself – told me to order a beer. Lisa was next to me, and I think I ordered a Corona because Mexican beer was about all I lived on in my early 20’s. Lisa bragged about my ability to freestyle and Cookie then stared me down, took a long pull off his beer and asked me to “do something impressive.”

It was on. Was he serious? I nearly froze. I was unsure of what to do. Should I recite some lyrics? Tell him some song ideas? I wasn’t sure. Instead I rapped off the top of my head to the cocktail waitress.

“Come here now for a second Miss blondie/ Any chance you wanna get on me?/ You live in LA? I’m from Arizona/ Do my boy Cookie a favor – another Corona?/ Don’t mistake this – I Cant fake this – you’re so hot for a waitress/ Do ya have fake tits? I cant tell/ That’s alright, I still think yer swell/ My name is Zachariah, how do I look?/ Trying to rhyme for this dude named Cook/ Ill steal yer heart like a bona-fide crook/Ill take yer naked photos and put em in a book/ So lets just let this relationship bloom/ So here’s the key to my hotel room…”

The waitress smiled. Cookie looked at me and said, “I want to capture THAT in the studio.”

I made out with the waitress that night.

So a week later, we were in Cookie’s studio, known as “LeftSide.” I had written a song in Las Vegas with my friend Jason Jacobs called “Runnin’ Shit” about two guys who slept with girls, traveled to Mexico and Vegas on random Wednesdays – and got high and drove really nice cars. In reality, we were both Southern California Bar Mitzvah DJ’s. The last time I had been to Mexico was with my mother over a family Christmas vacation (typical Jewish trip – Mexico over Christmas) and I drove a 1989 Dodge Lancer.

To top it all off, I was desperately unable to do anything in the studio that night – but SUCK.

The studio was a small rented office space off of Slauson and La Cienega. Cookie hooked me up with a producer named Warrior – who was a master of the MPC 3000. We smoked some weed, made a beat and put together a silly rap song full of voice imitations and bad jokes and pop culture references. It was called “Come On” and I was convinced it was my ticket to the big time. A crossover hit… a massive smash. Cookie started marketing me to record companies as “If Eminem hung out at Dawson’s Creek.” I should have quit right then.

“Dawson’s Creek” meets “Eminem.” (Meets a beer gut). The author freestyling at a party circa 2001

I put out an EP on Q/LeftSide Records – and it went triple plastic. Every major label denied me. I ended up with a closet full of 3500 CD’s – which included a song called “Other Side” featuring the powerful voice of a silk-voiced friend of Cookie’s named Stacy Ferguson. Today she’s known a little differently. She’s Fergie from Black Eyed Peas. I never thought she had much of a future. She did have a voice from God, but so did a lot of girls. When we stopped hanging out, I didn’t think she’d go very far.

After LeftSide folded, I ended up starting a country rock band that dabbled in hip-hop. We had a little local success, but not much more. From there, I caught a lucky break and got on TV – where I was able to convince the folks behind the screen to let me attempt to record some songs for nearly every show I have been a part of. Today, those residual checks amount to roughly 63 cents a year.

I also recorded a bunch of stupidly silly comedy rap songs about Cartoons I’d like to F*%&, White People Problems and the TSA. I have released a few CD’s on some small labels and I have been hired by over two dozen companies to write and record rap songs for their products, from Levi’s Jeans to Netgear. So, I guess, technically, I once called myself a rapper… but I certainly never took it seriously. And now, the style of rap is so much different, I have no idea how to imitate lyrical geniuses like Lil Wayne and Drake. I’m still stuck in that Will Smith meets Skee Lo style. Storytelling, comedy and fluff rap.

According to my calculations, it had been nine years since I truly “battled” somebody. A battle is when you trade rhymes with another emcee, often including insults, braggadocio and clever wordplay. A lot of rappers suck at this. For some reason, I was always able to come up with quick rhymes. In fact,  I have never lost a battle in my life. Other fools have claimed they out-rapped me, but most of them recited something I could tell was written beforehand. I was strictly improvisational.

Freestyle rapping is like working out. You need to do it all the time or you get rusty. Rarely do you take nine years off and step up to the microphone and sound like Rakim. For some reason, however, last week – following a few glasses of red wine, I thought I was back in the Skybar in 1999.

The three dudes standing outside of the Smokehouse restaurant in Burbank were sharing a joint and rapping about “Maybach’s” and “Stackin’ Chips.” The valet parking attendant took our ticket as I caught one of the guy’s eyes. I guess in the 90’s you would call what he was doing “Mad-dogging.” I would normally run from any large crew of wasted black dudes in a parking lot at 11 o’clock at night, but for some reason, I felt the need to jump into the rap battle. Maybe it was because he kept staring at my wife and obviously commenting under his breath about her. Whatever it was, I felt like I needed to say something. I took a step towards them.

“Punk ass bitches get stitches like snitches/rub you out like a genie, grant ya 3 wishes/ Im a killa, son, drinking Miller, son – All the tracks on my album dope, no filler son…”

I heard the guy’s rhyme. Not bad, but I knew I could hang. I sort of stumbled over as my wife failed to pull me back and stop me from entering the cypher. As I walked up, they noticed me and rapped about my approach.

“White boy stepping up, what the fuck he want/ Gonna kick him in the dick if he pull a stunt…”

The 3 guys laughed uproariously. I started getting nervous. I heard my wife gasp. The other couple we were eating with immediately signaled for their Volkswagen Touareg to be ready to drive off should I get into a street brawl or something. I slipped up to the crew of rappers.

“Are you guys rapping?” I asked, realizing I sounded like that fat pledge in Animal House asking the frat brothers if they were playing cards.

They burst out laughing. I thought I was doomed.

“Yeah, you wanna step in?” A large man with a diamond encrusted grenade-chain offered.

“Well, I actually freestyle… was hoping to get in on the cypher.”

More laughter. They punched each other’s shoulders and leaned their heads against one another.

“Are you gonna put your doggie bag down first?” One of the guys asked.

I looked down. In my hand was a plastic bag of leftovers with a red bow around it. I looked like the schlub I used to make fun of when I was younger. The out of touch chump who was taking home half a New York Strip and three pieces of cheesy-bread after a double-date night. I knew the only way out was to rap. I began firing.

“Yo -I take a bag of leftovers from the smokehouse/ you can continue with your jokes now/I’m broke now – so I have to eat this for breakfast/ When’s your next concert? Put me on the guest list/ I spent my weed money on my wife’s gold necklace/ That’s her over there, she’s got the Best Tits/ I’ve ever seen and they aint even fake/ We live in a house over in Toluca Lake/ I bust freestyles in only one take/ Put the kids to bed stay up late and get baked/ and I know I look lame and somewhat old/ You guys look like a younger De La Soul/ But my wife’s calling me to get the car and go home/ Because she don’t want me to catch another cold/ So I’m out – thanks for giving me time / I doubt any of ya’ll can defeat that rhyme!”

I stepped back and took a breath. Wow. I had dropped 16 bars in front of a crew of three hardcore hip-hop heads who probably took rap music more seriously than I ever did… I had held my own. I was proud and I looked back at my wife and the other couple, who were stone-faced and somewhat impressed. Wait until I tell my son about this!!!  I thought to myself.

And then one of the guys began answering my challenge. His name was Black Angus.

“Yo, white boy – your white noise aint right boy/ yeah I see yer wife, she no longer tight, boy/ cause I did her last week/ in the back seat of my Jeep/ Did it in five seconds without a peep/ while you was asleep/ getting kids ready for school/ I gave her my tool and took a piss in your pool/ Smoked your bullshit weed/ pulled it indeed/ Killed you like Drago did Apollo Creed/ Planted a seed – inside her – you mind?/ Now you wonder why your kid looks like mine?/ Don’t step into my circle unless you bring skills/ go home to your anti-anxiety pills/ Watch whack white TV like that show the Hills/ and keep being a sucker and paying yo’ bills/ You a dumb-ass honky who cant rhyme for shit/ Now go back to your Minivan before you get HIT.”

The crew cheered. Our friends Touareg sped off and I was silenced. A terrifying chill, like one I’ve had on airplanes when we hit some odd air pocket that scares even the flight attendants, engulfed my body. I was smoked. Forget winning a freestyle battle, I had been pulverized, insulted, dissed and clowned by a dude outside of a steakhouse that I would probably never be able to go to again. I faked a laugh, and tripped backwards towards my wife and our awaiting car. Which, by the way, is NOT a Minivan.

“How’d that go for you?” My wife asked as we raced off into the Burbank night.

“Uhm, not well,” I said.

After five minutes of complete silence, I uttered my final words of the incident.

“Why’d they have to be so mean?”

The Smokehouse. Many a Hollywood deal has been brokered here. And at least one embarrassing freestyle rap battle.

I sulked into my home. Being a little buzzed, I passed out watching SportsCenter and the thought of rap music sickened me with every commercial starring Andre 3000 or Ice Cube. It was a cold bucket of water to the face that reminded me that I am – at best – an above average rapper. I am a decent freestyler, but in no way cut out to be a professional. Bottom line? I am too much of a pussy.

The next morning, I pulled out the leftovers from the Smokehouse and considered making a steak-and-egg omelet. The one indulgence I was going to allow myself. When I saw that half of a New York Strip in the bag, it brought back too many bad memories from the night before. I tossed the meat in the trash and settled for a bowl of Trader Joe’s ‘Honey Nut O’s’ instead.

That afternoon, the new Rolling Stone arrived.

Fergie was on the cover…

– Zach Selwyn, September 12, 2012

Other Side        (Click to hear Zachariah “Other Side” featuring FERGIE)

Buy the MP3 HERE!!

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