[EXCLUSIVE INTERVIEW] Comedian Zach Sherwin’s Last Laugh: D*ck Pics, Kinky Sex & A Secret Love For Rihanna

In Last Laugh, MStarsNews talks to our favorite comedians or funny people about some of the last experiences they've had over the years. For this installment, we welcome in comedian Zach Sherwin.

Rapping in itself is an incredibly difficult art form. Being both creative and funny in your lyrics, however, appears to be an even harder feat to accomplish. Yet, somehow, comedian-rapper Zach Sherwin seems to have done both rather swimmingly. For years, the artist has been shelling out incredible beats alongside some insightful yet oh, so comical lyrics –– whether they be in his own songs or during feature appearances on the likes of Epic Rap Battles of History and other inspiring platforms.

Amid all of his accomplishments, Zach Sherwin recently made a stop over to have a Last Laugh with MStarsNews.

So, Zach Sherwin, who/what/where/when was the ...

MStarsNews: Last time you wore something you hated?
Zach Sherwin: My mom's retirement party in May. The career she was retiring from: rabbi. The party was in the small Missouri town where I grew up from age 12 to 18, and all the other party guests knew me as the Rabbi's Son during that incredibly awkward phase of my life.

I still dress like a man-boy and don't own appropriate attire, so the day before I left LA for the party, I went to a thrift store and bought ill-fitting clothes that smelled bad and made me sweat, which I am also doing as I type this and remember how uncomfortable I was, both socially and sartorially.

MS: Last person to see you naked?
ZS: My girlfriend. That sounds like a boring answer, but we have an exciting sex life, so it's actually not boring. And if you're bored, reader, feel free to entertain yourself by imagining exactly what "exciting" might mean, and wondering whether my definition is more or less crazy and kinky than yours. (Disclaimer: I haven't seen the GF since yesterday morning, and I can't rule out the possibility that in the meantime, some previous flame may have taken a fond nostalgic look at some long-ago naked picture I sent her, and if that has indeed happened, then SHE is the last person to see me naked, whoever she may be. I like sending dick pics so there are many candidates.)

MS: Last day job you had?
ZS: I used to tutor kids for their bar or bat mitzvah when I first moved to LA. Remember: rabbi mom. Grew up with the skill set. In my DNA, y'all! Shalom.

MS: Last place you traveled to outside of the US?
ZS: Montreal, for the 2014 Just For Laughs festival. While I was there, I ate vegan poutine for the first time. It's ironic that "poutine" begins with the word "pout" when it makes me and others beam with joy.

MS: Last guilty pleasure you discovered?
ZS: HA. I immediately thought of a very specific answer to this question but it's WAY more personal than I'm comfortable revealing. OH MAN, you guys would love it though, and you would judge the shit out of me, and probably a lot of you would check it out yourself. Instead of telling you what it is, I'll say: working my way through Rihanna's entire catalogue a couple of months ago. That's my guilty pleasure. Doesn't that suck? I know. It's infinitely less juicy than the thing I'm not telling you. Sorry!

MS: Last piece of advice another comedian ever gave you?
ZS: "Start freestyle rapping on stage." –– my buddies Micah Sherman and Myq Kaplan. And I've been doing it! Mixed results.

MS: Last thing you regretted?
ZS: I ordered a whatever red curry at a Thai place in Culver City CA; a friend got the spicy mint noodles and he let me try a bite. Ignorance would have been bliss. They were immeasurably better. I'm actually still pretty broken up about it.

MS: Last time you bombed onstage?
ZS: August 25, in Venice Beach. Such a bizarre experience. At one point a dog trotted through the showroom and no one batted an eye (although many of the audience members appeared to have undergone extensive plastic surgery that would have made it difficult to move individual facial features). I actually had a pretty good time pointing out how weird everything was about that show and don't think I bombed, but it would definitely be understandable if someone watched a tape of my set and characterized it as bombing.

MS: Last time you lost your cool?
ZS: The other night I was biking around town and a guy in a Hummer SUV (autofill "douche") drove by and yelled, "Watch out!" at me –– I guess in an attempt to startle me and in hopes of making me fall off my bike? Ugh. I was furious and pedaled as hard as I could and caught up to him at a red light and just stared at him and shook my head and then worried he was going to run me over when the light changed.

If that ever happens again, though, I know exactly what I'll do: sneak up next to the open window at the red light and yell "WATCH OUT" from inches away and then pedal off down a side street.

MS: Last piece of advice you gave someone?
ZS: If you're getting an Uber from LAX, they can't pick up at arrivals, so just take the first off-airport hotel shuttle that comes along and then call the Uber from there. And make sure it's an UberX! The regular ones are way too expensive. You're welcome, Angelenos and visitors.

MS: Last time you were the butt of the joke?
ZS: I did hallucinogenic mushrooms with two buddies recently, and we were sitting on a dock by a lake when I moved my chair to get a better view of the natural surroundings but didn't realize the chair was attached to the dock with a rope. So it didn't go anywhere but I kind of fell over. My friends laughed and I started laughing too because when you're on mushrooms, you understand that we're all one. One giant butt.

MS: Last time you got into a fight?
ZS: Summer camp, when I was ten, with Michael Ginsberg. I guess I won? It ended with me sitting on top of his back and punching his shoulder blades while we both cried.

MS: Last time you wished you were someone else?
ZS: I don't think I do this very much. I guess I would like to instantly become someone who had achieved an inner state of calm, quiet, and peace, like the Dalai Lama and a few people I know seem to have done, but I understand that part of being that kind of guy is not wishing you would spontaneously turn into someone besides yourself.

MS: Last thing you had to apologize for?
ZS: Going to search for "sorry" in my e-mail inbox – hold please ... OK, I'm back. Pretty boring. Mostly apologizing to people for not calling or writing them back sooner. I'll say this: last week I read a Neil Gaiman book in which he quoted someone saying, "Never explain. Never apologize." I've been trying it out and it's pretty fun so far.

MS: Last time you laughed really hard?
ZS: Watching episodes of Nathan For You while stoned. I do drugs less than one might conclude from reading my answers. Then again, I don't not do 'em.

MS: Last time you felt uncomfortable?
ZS: Last night I was at the Hollywood Improv talking to a friend who is black, and a drunk stranger who neither of us had ever met came up and started freestyle rapping at my friend and exhorting him to join in. It was definitely happening because my friend was black and because the stranger, who was white, thought that all black people rap. Very anxious-making. And the guy was rapping about bitches and hoes. It was just awful. That is not the kind of freestyling I hope to do more of onstage.

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