Artists Creating Entertainment and Jill Benjamin Events brought Zach in to freestyle for multiple offices in the LA area for Valentines Day, 2024…
Tag: freestyle
Zach releases EP of Comedy Central / Film songs from 2009-2011
Zach is finally releasing a collection of songs never available to the public before via itunes! Most of these songs are from the SELWYN BROTHERS series of videos done for Comedy Central from 2009-2011 – but also included is “Im in Edukashun” from the film “Lower Learning…” Check it out!
CLICK HERE TO BUY CHICK DRINKS
TRACK LINEUP
2. Chick Drinks
3. Hello, Beautiful Homeless Girl
4. Recession
Watch Zach’s perform a freestyle country rap song w/ his band!

Zach’s Band to Play 10-Year Anniversary this weekend at Pappy and Harriets!

THIS SATURDAY!!
MAY 18 – 9:00 pm – PAPPY AND HARRIET’S PIONEERTOWN PALACE – We return to the scene of the rhyme… Drive out to Joshua Tree, get a hotel room and join us!!!
53688 Pioneertown Rd Pioneertown, CA 92268
With the LOBOS RIDERS and SPECIAL GUESTS!!!
Also, CHRIS LATERZO & Buffalo Robe

Watch Zach and Jingle Punks do a cover of “F***kin’ Problems” by A$AP ROCKY!
Warning * NSFW

2 Scarves – aka Waylon Nimoy and Ca$h $hatner
Recording their new cover of “F***kin’ Problems” by A$AP ROCKY
Read Zach’s New Short Story, “Honeysuckle”

There is a small stretch of road about five minutes from my house that is known as “Tranny Alley.” The section I am talking about exists on what used to be the most famous highway in America: Route 66. Nowadays, it is known simply as Santa Monica Boulevard and it famously runs the length of the city, cascading into the Pacific Ocean at its conclusion.
“Tranny Alley” gets its name from – you guessed it – the number of transsexual prostitutes working their trade up and down the boulevard. Situated directly between Highland Avenue and Las Palmas, the majority of these prostitutes seem to use a shop called “Donut Time” as their home base. It was here, at this Donut Time, that I found myself picking up a 28-year-old prostitute named “Honeysuckle.”
Any man who has lived in the city of Angels for any period of time has found himself staring at a tight pair of denim shorts walking down the street only to be surprised when the person turns around and reveals him/herself as a guy. Santa Monica Boulevard is usually the place where it all goes down. Sometimes, they catch you staring and send an awkward wink your way at which point you react by either looking the other way or thinking to yourself, Wow… Dude or not, I still got it!
Last week, when I was on my way to pick up my six-year-old son from school, I noticed a pair of those exact denim shorts parading across a parking lot directly in the heart of Tranny Alley. When the person turned around, she had caught my eye – and sent a gorgeous and flirtatious look my way. I watched her cheetah-strut her body towards Donut Time, where she adjusted her top and threw me a salacious wink. I was stunned. She was by far the prettiest girl I have ever seen in Tranny Alley in the 19 years I have lived in this city –and there was even something familiar looking about her… but I couldn’t quite place it. Needless to say, she had an incredible Rihanna-like body with a face like a younger Sage Steele. (ESPN anchor). If she was, in fact, a man – I didn’t care… She was worth making eye contact with.
As I scooped up my six-year-old from school and we began driving home, I decided to take Santa Monica Boulevard again, risking a Donut Time drive-by, knowing fully well that my son often screams out “Donuts!” whenever we pass a shop serving up the fried, round, sugary treats. Giving your kid a donut at 3:30 in the afternoon is a terrible idea, as it often leads to a sugar crash, Lego’s being thrown all around your house and a dinner time screaming match between me and my wife… However, the moment I passed the shop, I noticed Rihanna again… She noticed me as well. She gave me a subtle nod and caught my eye in a flirtatious way, just as my son yelled out at the top of his lungs,
“Donuts!”
I flipped on my blinker and made a left turn into the parking lot.

My initial intention was not to speak to her. I wanted to get inside the shop, pick out a donut, maybe get a closer look and then speed off towards the park to make my son run off the 550 calories he just inhaled. Instead, she approached me like a long lost girlfriend just as I walked through the door.
“You go to the Hollywood YMCA, don’t you,” she asked as I cradled my son so he could get a better look into the donut case.
How the hell did she know that?
“Uhhm, yeah?” I said quizzically. “Are… you a… member?”
She laughed. I took a quick gaze at her throat. It was Adam’s apple – free.
“I shower there sometimes,” she continued. “I’ve seen you and your kid walking around.”
It was then that I put it together. She was a member of the Hollywood YMCA. I had seen her before, striding around the ground floor, making every pasty-white mother of three uncomfortable by flaunting her ferocious curves and Olympian build. I always had assumed she was a personal trainer or a professional fitness model or something… Looks like she was simply, just a professional.
“Are you a…” I started, before looking down at my son, knowing that no six-year-old should be conversing with a prostitute ten minutes after leaving Math Workshop.
She smiled and rubbed the side of my shoulder.
“I can be anything you want me to be.”
Now I have never been one for talking dirty, but for some reason, her comment uncoiled some inner beast in my loins that had been lying dormant for way too long. I noticed a boulder-like erection burst into my boxer briefs that felt like a Sumatran rhino giving birth. I wasn’t quite sure what it was… but this girl’s voice and body and face were so searing, for that one fleeting moment I truly, deeply in the back of my head, considered throwing away a perfect marriage to the love of my life – consenting to spending the rest of my adulthood couch-surfing in Van Nuys. I felt contented with the fact that I would rarely be allowed to see my children again… And if my wife wanted to take half of all my finances? FINE. These all seemed like worthy sacrifices for one night of rapture with this thunder-bodied beautiful sex bomb who looked like she could break my penis off.
And who may or may not be a guy.
I paid for the donut and did my best to shake off the fantasy. As I allowed my erection to lower itself to half mast, I eeked a smile her way and raised my hand, showing her my wedding ring, as if to say, “Sorry, I’m married.”
She laughed and whispered into my ear.
“Single men don’t walk into Donut Time,” she said. “Most of my regulars are married… But you’re the first guy who actually brought his kid along.”
Yeah, about that… I looked over at the boy, eating his chocolate sprinkled donut, unaware that his father could be 20 minutes away from making the biggest mistake of his life. Unaware of “Tranny Alley.” Thinking only of toys and ninjas and the Angry Birds Star Wars toy on his Hannukkah list. Just innocent, pure and happy…
“It’s 50 bucks for a blow-job,” she whispered.
“We should go,” I yelled out to the boy. “C’mon, dude…”
I loaded him up into the car and didn’t even buckle his seat belt. His face was smeared with chocolate. Within six minutes, we were up in the park and he was climbing a play structure as I found myself perversely Google–searching “Sexy Rihanna Photos” on my iphone. Had anybody seen some of the half-naked images I came across, I would have been arrested and thrown in prison for lewd conduct. Looking at soft-core porn on your phone in a public park is probably a bigger offense than actually picking up a prostitute… (I looked that up by the way… It’s not.)
Paranoid, I cleared my history, turned off my phone and did 10 pull-ups on the monkey bars as a way to release some unbridled energy.
I believe I first realized that I didn’t have my wallet about 45 minutes later. We had come home from the park and the Rihanna incident was way beyond me – because by that point, other concerns popped into my head. What time was his soccer practice? Did I forget to email the bank about the house Re-Fi? Why did I forget to buy printer ink? But now, something even more horrifying had crossed my mind: My wallet was gone, and the only place it could possibly be was sitting on the counter at “Donut Time.”
When my wife came home, I told her I had left my wallet at my son’s school and I had to go get it. She called me a dumb-ass and told me to hurry up. After all, we had Nick and Marcy coming over for dinner. I jumped in the car and raced towards Santa Monica Boulevard as fast as I could, praying that Rihanna was nowhere to be found and that my wallet was safe and sound behind the counter. The drive over there shared the same nerve-wracking feeling of a first date in high school… It was mortifying.
As I began creeping along towards Tranny Alley, I noticed that there were a few more ladies of the night walking the street. Most of them were obviously men, and I avoided their looks as long as I could. I managed to find a parking spot at a meter, hoping my presence would go unnoticed. I crossed over the sidewalk and ran towards Donut Time at a swift pace. When I got there, I grabbed the door handle and pulled it open. Before I could slide inside, a familiar voice turned me around.
“Looking for this?”
There was Rihanna, holding my embarrassing tri-panel Velcro piece of shit wallet with a clear sleeve for my driver’s license and a change purse zipper. My driver’s license was in her left hand.
“Zachary Stephen Selwyn, huh?” She said. “You look younger than 37.”
“Uhm, thanks,” I said, not knowing if she really meant it or if it was her way to talk a potential john into dropping 500 bucks on life-ruining sex.
“Where’d you, uhh – find it?” I asked.
“I can find a man’s wallet anywhere. Now you want it back, or what?”
“Yes please,” I meekly answered.
“You can have it — if you run me up to the YMCA – I have to take a shower.”
The first thing that popped into my mind was the Hugh Grant – Divine Brown incident. Back in 1997, Grant was a superstar who was arrested for receiving fellatio in his BMW just north of Tranny Alley from a prostitute named Divine Brown. Following the arrest, Grant’s reputation went from ‘irresistibly charming leading man’ to Mickey Blue Eyes. Divine Brown, meanwhile, has allegedly made close to two million dollars from personal appearances and pornography and is now raising her three well-off children in Beverly Hills…. Advantage: Prostitute.

The other famous incident at the time was when Eddie Murphy was pulled over with a tranny prostitute in his car in the same neighborhood. Although never charged with anything, Eddie has been dragged across the floor by the press since then as well. By offering Rihanna a ride, I was risking my career and more importantly, my marriage. It seemed like a no-win situation…
“Sure, I can give you a ride,” I said.
I wasn’t sure why I had agreed to do it. Part of me believed it was a moment of weakness where I felt like the character “Mr. Incredible” from the film The Incredibles. Downtrodden, bored and eager to find adventure again, he takes on paid missions without his wife knowing -which, at first – get him his mojo back. Of course he ends up nearly dying until his superhero family arrives and saves his ass with superpowers and they all live happily ever after. I wondered to myself if my superhero family would come save me should I get arrested with a prostitute in the front seat of my car… My initial thought was, probably not.
Rihanna handed me my wallet and tried to hold my hand as we walked back to my car. I pushed it away and kept my eyes peeled for any sign of police. At the moment, everything looked clear. We got in and I quickly lowered my radio so she wouldn’t know I had been playing the Rihanna song “What’s my Name” on my ipod for the past 30 minutes. We slowly pulled out into traffic and headed up towards Vine, where I would shuttle her to the awaiting, lucky, pulsating shower beads of the Hollywood YMCA.
“OK, you know my name… what’s yours?” I asked her. After all, I couldn’t keep referring to her as “Rihanna.”
She took a moment to fiddle around with a pair of my sunglasses I had resting against the center console. She put them on her eyes and turned towards me.
“You can call me Honeysuckle,” she said.
Perfect. Honeysuckle? Could there be a more appropriate name for this fiery African-American fuck machine than “Honeysuckle?”
“Is that your real name?” I asked.
“Is Zachary your real name?”
“Uhh, yeah.”
“Than my real name is Honeysuckle.”
“Wow!” I said. “Like the Willie Nelson film Honeysuckle Rose!”
“I’ve never heard of that.”
As she lowered the passenger side mirror to apply lipstick, I found it odd that she was on her way to take a shower and was applying make-up 10 minutes beforehand. She pursed her lips and laughed at her face in the mirror in a way that exuded more self-confidence than any woman I feel I had ever encountered. It was the last thing you expected a “soiled dove” to be doing. I dug deeper. Fascinated by this workhorse of sexual pleasure. I have always been obsessed with those who spend their lives this way… I love their back-stories and their ideals and hearing about the unique way they view the world. Her story was enthralling
As it turns out, Honeysuckle was born and raised in Oakland by a single mother who was also a prostitute. Honeysuckle had dropped out of high school at 16 when she got pregnant, and had lost the baby during childbirth. Disenchanted with everything, she moved to San Francisco were she began turning tricks for as much as $1500 a night. By 21, she was well known throughout the city and pleasured star athletes, politicians and businessmen from all over the world. She had even once been flown to New York for a convention with top brass at a massive electronics company that we all know about. Finally, she settled in LA, where she heard she might be able to work as a high-class call girl and not a “streetwalker.” Unfortunately, most of the girls in Los Angeles who were in that racket were five to ten years younger and from foreign countries. Honeysuckle claimed she was too street savvy to get caught up in that business and she now walks the boulevard three times a week, doing what she can to keep her lights turned on, her weave silky and her body in shape. It was a story straight out of a terrible movie. A hooker with a heart of gold… I wasn’t sure what I believed.
I had one more question I had to ask her. I took a chance.
“So, by any chance… are you a transsexual?” I boldly proposed.
“Honey, please – I am all woman,” She exclaimed. “You know what my father once told me before he split on me and my mom? He told me the best piece of advice I have ever heard. He told me “As long as you got a pussy, you will never go broke.”
I took that in. I have absolutely no plans of ever sharing that advice with my two-and-a-half-year-old daughter.
We drove in silence for a few blocks as she applied more makeup and drank from a mini bottle of grape Five-Hour Energy that was tucked away in her purse. I was only hoping I could make it to the destination without being pulled over by any flashing red and blue lights. As we made a left onto Selma near the new Trader Joe’s, I finally broke the silence.
“So, why do you belong to the YMCA?” I asked.
“The Y lets homeless people in on a 10 dollar -a-month discounted rate,” she explained. “I’d say 50-100 YMCA members are homeless people or hookers… it’s true. Trust me, do NOT go in the jacuzzi.”
All I could think of was the fact that I had taken my six-year-old boy in the Jacuzzi two days earlier.

When we wound up pulling up to the front of the YMCA, it suddenly dawned on me that I had seen a number of toothless men in the locker rooms, shady looking women emerging from the massage rooms and occasional clove-smoking dope fiends shuffling in and out of the front door. Maybe Honeysuckle was telling the truth… The Hollywood Y was as much a gym, a gravity strength pilates class and a Kids Klub, as it was a homeless shelter… I was about to cut my engine when Honeysuckle instructed me to pull to the side of the building.
I did as I was told, now fully aware that the earlier rhino boner I had set fire to had now completely retreated inside of my body. I pulled my car into a metered space and watched her smooth out her shorts so they wouldn’t bunch up. She casually stared back at me with her hazel-ish eyes and put a tethered hand on my upper right thigh.

“The best thing about a woman like me, Zachary, is that I don’t kiss and tell,” she said.
I looked deep into her pooling retinas. She was marvelous. A physical specimen. Probably no older than 27 or 28. Any man with 100 or 200 or 500 dollars was sure to have the time of his life with this woman – but I was simply not going to be that guy. All I could think of was my son and the chocolate smeared across his face and his Hannukkah list and my wife’s smile and my daughter’s growing Hello Kitty collection. I was even looking forward to a small argument about getting the boy a donut at 3:30 in the afternoon.
I just wanted to go home.
Honeysuckle kept her hand on my thigh. I thought long and deep about how I was gong to let her down… I didn’t want to crush her. I mean, her life had been so hard, could she handle my rejection? How would she react? I was nervous. I took a deep breath and reached down into the depths of my soul for what was the honest-to-God truth.
“Look, I’m flattered… but I – I can’t – I could never live with myself,” I said.
Without flinching, her hand was gone from my leg. She clicked her tongue against the roof of her mouth and opened the door. Within eight seconds, she had dismounted my car, tossed her weave back over her shoulders and buckled her purse.
So much for her having trouble taking rejection, I thought.
As she walked in front of my car towards the YMCA, I was watching her denim shorts again. It was then that she turned around and ran back to my window. I knew it… I thought. She couldn’t stand to think about how this 37-year-old father and husband had turned down her advances… She couldn’t fathom being rejected or humiliated like that… I KNEW IT! In fact, what I was thinking was, I still got it…
As she persuaded me to roll down my window, I expected another come-on. After all, getting hit on by any woman at my age is flattering, even if they turn out to be a prostitute… I zapped down the pane and awaited her final cry for my love…
“Hey, Zachary,” She began. “You had 50 bucks in your wallet when I found it, so I took it as a finder’s fee… OK?”
She pirouetted and slinked towards the awaiting doors of the YMCA.
I’ve driven by Tranny Alley a few times since, but Honeysuckle seems to have disappeared. I hadn’t seen her at the YMCA either, until earlier this week. I caught her bounding out of the locker room, midriff showing, with micro-beads of sweat glistening just above her belly button. As usual, all the YMCA moms stopped and stared, aghast at her sheer physical presence and beauty, and the older dudes working out on the machines snuck glances as she sauntered towards the door. As she passed by my son and I, she caught my eye and gave me a silent nod. It was all unspoken and perfect and it made me feel comfortable and happy knowing that she was still around and had no intention of changing who she was to appease the eyeballs of others. Only one thought entered my mind as I watched her move through a crowd of bewildered onlookers.
Best 50 bucks I ever spent…
COME SEE ZACH PERFORM LIVE AT THE HAYRIDE! Tues. Dec 11 – 7:30 pm. BOOTLEG THEATER!

Zach to perform “How to Get a Medical Marijuana Card” LIVE on Swedish Late Night TV tomorrow!
Sweden TV4’s late night talk show will feature ZACH singing his counter-culture anthem “How to Get a Medical Marijuana Card” LIVE on tomorrow’s broadcast. We’re betting most of you dont live in Sweden… So come down to the W Hotel in Hollywood at 10:45 a.m. and watch Zach perform it LIVE!
More about the show: http://www.tv4.se/jenny-str%C3%B6mstedt
Download the song HERE
Watch a crappy YouTube video of the song below!
Read Zach’s New Short Story: “The Freestyle”
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 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.”

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.

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.

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?”

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)
Come see Zach live at the Irvine Improv all Weekend with JOHN HENSON!
Zach is joining Wipeout host/comedian JOHN HENSON all weekend at the Irvine Improv for 4 nights of insanely funny comedy. Also on the bill are the very funny HALLI BORGFJORD http://halliborgfjord.com/
and ROB O’REILLY http://www.imdb.com/name/nm2688418/
September 6,7,8,9 -Irvine Improv with JOHN HENSON and FRIENDS (The TV HOSTS of Comedy!)
Please CLICK HERE to buy tickets!!!!!
See Irvine Improv website for more information. 6 SHOWS!!!
Watch Zach’s Freestyle Rap from the Bacon Bacon Truck in San Francisco!
Zach was invited up to San Francisco last week to drop some freestyle rhymes about the world’s greatest food truck: BACON BACON. He rolled in , borrowed a guitar and made this up on the spot – ENJOY!
(directed by Miles Steuding)
LINKS to BACON BACON TRUCK
twitter – @baconbaconsf

























