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.

“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:

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…

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…

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.

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.

“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.”

 

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.

“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…