Comedian and Desus & Mero Writer Josh Gondelman Takes Shots, Talks Working for John Oliver || SYS

– Now all I’m thinking
are the words gravy shot to the tune of “Baby Shark.” – Gravy shot!
– And it is truly destroying my life.
– Oh, you mean gravy shot, shot? – Do, do, do do.
– Are we gonna get sued? (upbeat music)
– From the basement of a pretty normal office
building in New York City, it’s “Shoot Your Shot.” Thrillist’s boozy trivia game show, with your host, Wil Fulton, and special guest, Josh Gondelman. Cheers! And remember to tip your bartender. – What’s up everyone? Welcome to “Shoot Your Shot.” I’m your host, Wil Fulton. Today, I’m here with Josh Gondelman, writer, standup, author, now working with Desus
and Mero on Showtime. How are you today? – I’m great, how are you? – I’m good, I have to ask you something. When was the last time
you took a bunch of shots? – Ooh, probably about two
years ago at a concert. – Wait, so you haven’t
taken a shot in two years? – No, no, no, that’s the
last time I took shots. – Oh.
– I’ve taken a shot, but it’s usually, that’s when you’re like, glug, nights over and then
I just like leave the bar, and get in a cab. – Oh, you know what this
show’s about, right? (laughing) – Yeah, yeah, yeah, yeah, yeah. – All right. It’s about taking shots. – Absolutely. – This shot is called
the Gond with the Wind. – Great.
– It’s got your name. – I know, it’s a pun on my
name that I haven’t heard much, which I like. – Gonna ask you a bunch of questions, You get the questions
right, I take a shot. You get them wrong, you take a shot. It’s as simple as that. Ready?
– I am, Sam. Let’s do it.
– First question, so I know you grew up in Massachusetts. – I did.
– Great state. I wanna ask you a question about Boston. How many people died in the
Great Molasses Flood of 1919, AKA the Boston Molassacre,
which is a way better name. – Very disrespectful to the dead. – Literally been 100
years, I think we’re okay. A, 19. B 21, C 33, or D no one died, it was a cover up. Hot molasses can’t melt steel beams. – See, this is the thing
about these questions, is that they’re tailored to
me, so it’s double embarrassing if I don’t know them.
– I would say quadruples. – I’m gonna go with 33 ’cause
that’s Larry Bird’s number. (laughing) – That’s why you picked it?
– Yeah. (laughing) – No, it’s B, it’s 21
people died in a giant 40 foot wave of molasses. – So do I just do this now? – You could, yeah. – All right.
– I recommend not storing them. – All right, well there we go. – Did you think it was okay? – Yeah.
– It’s not bad, right? – No.
– You are commonly known as the nicest person in showbiz. There is this common Mass-hole stereotype, and you grew up in Massachusetts, right? – Sure did. – How did you buck that and become, by all accounts, a nice guy? – I still have some very
Massachusetts tendencies. The kind of like– – Like punching people
in the face? (laughing) – Yeah, a lot of punching
people in the face, but I do it so gentle. I have the posture and density of a croissant, but I still have these hardened,
like when I’m in traffic, it’s a lot of like are you shittin’ me? And I’m like, oh, that’s in me. – You’re just throwin’ iced
coffees from Dunkin’ at people. – Oh my gosh, I would never
waste a Dunkin’ iced coffee. (laughing) – You are from Massachusetts! – Yeah, I drink Dunkin’ Donuts iced coffee every day of my life. – Get this man a deal.
– Please, Dunkin’ Donuts, give me lots of money. I swear to Christ. (beep) – And you were a preschool teacher? – I taught preschool for
four years after college, and I was like an assistant
at early childhood programs before that. I taught elementary school
Spanish for two years while I was in college. I was deeply unqualified. – (laughing) Do you speak Spanish? – I was a Spanish minor, so I knew more than kindergarten students. – Amazing. Do you have any pre-k friendly jokes? – Why didn’t the skeleton cross the road? He didn’t have the guts. And then, how do you make a tissue dance? You put a little boogie in it. – Did you like being a pre-k teacher? – I did, I really liked it. It was just a very encouraging
way to spend the day, especially when I knew I was gonna go out and do comedy after. – Was it hard to work up the motivation to do something you love
even with a day job? ‘Cause I think a lot of
people struggle with that. – I really liked it. It was fun for me, it was where my friend, a lot of my friends were at that time. And by the time, also, I was teaching I had already been in comedy long enough that I was regularly booked. I was just like okay cool,
this is another part of my day. – That’s awesome. My mom’s a pre-k teacher. – Oh, that’s wonderful. – Barney, noted purple dinosaur. You know him? – I mean, not personally. (laughing) – Barney was originally meant to be what instead of a purple dinosaur? A, a blanket. B, a Dalmatian. C, an alien. D, a gentle ex-convict
with a heart of gold. – I’m gonna go with C, an alien. – Guess what? It’s A, a blanket. (laughing) – No way!
– I swear! – That stinks.
– My shitty internet research. – How long was it like,
what if it was a blanket? And then they just beat the (beep) out of that guy. Was that how long it
was gonna be a blanket? – They held it, the
brainstorm in a town hall. People were just yelling stuff out. – What if it was a blanket? What if it was just me? – No, it was a blanket, but
then, Sheryl Leach, the creator was like well that would be too hard. Her kid loved dinosaurs, she
put two and two together. – I don’t even think it was two and two. I think she put one together, and was like this stinks
we’re changing it. I refuse to drink this shot. This is a protest shot. (beep) There’s no way it was seriously considered that Barney would be a blanket. If someone brought that up in a meeting, they’d be like there’s no
bad ideas in brainstorming, except that one and you have
to go to jail, you weirdo. So this shot is being taken under protest. My bloodstream should know to reject it. (laughing) – Blankets are nice. (shot glass taps table) – I love a blanket. – This next one, it’s called Risk It for the Biscuit. We have a little cocktail
of human edible dog treats. Whoever gets the question wrong– – This is, okay.
– Instead of a shot, you get to (laughing)
try one of these out. You have a very well publicized adoration for your senior pug, Bizzy. What is a group of pugs called? Like, you know, a pride of lions? – Oh this one I know!
– Do you? – Yeah, oh yeah, I can do
it without the options. – All right, fine. – It’s a grumble.
– Yeah, you’re right. Now I have to eat this.
– Yeah, man. – (laughing) That was a ringer. – I know.
– Doesn’t this one look like someone ran
over a chicken nugget from McDonald’s? (laughing) – It does. I thought it looked like
little dog brass knuckles. (laughing) Little dog knuckles tattoos. Ruff. (laughing) How is it? – It’s real bad. – Yeah I bet. That’s for people.
– You wanna bite? – No!
– It’s just bad. – Yeah. – Question number four. I’m asking about this ’cause
I love your Esquire piece about the Tough Mudder. – Thank you. So, I ran a Tough Mudder. – Sponsored by Wheaties?
– Sponsored by Wheaties. They truly were like we
usually get the best athletes, and try to inspire people, and we thought we’d try
something different. (laughing) – That’s insane. It’s like Michael Jordan, Bruce Jenner, you. So I have a Tough Mudder
centered question. Which of the following is a real obstacle on a Tough Mudder course? – Okay. – A, the Arctic Enema, B, the Belly Flop ‘n’ Slop, C, the (beep) Twister or D,
the Chemical Castrator? – It’s definitely not the last two. – Are you sure?
– Yes. I’m gonna go with A, Arctic Enema. – That’s right.
– Thank you. – All right. The coldest enema you’ll
ever have, they promise. – (laughing) It’s not a good promise. – (laughing) No. Okay. Mm. (licks lips) Question number five,
Hot Takes or Shot Takes, we’re gonna ask you
kind of a tough question to test the limits of
your nice guy persona. – Hot Takes or Shot Takes. – If you don’t answer, that’s fine, but you have to take a shot. If you do answer, I have to take a shot. – Okay.
– To commend you. Who is a celebrity you’ve
met where you’re just like, ah man, that person’s an asshole, and I wish I never met this person? – I’m trying to think if
there’s anybody that was bad, bad and there wasn’t. I think all the people that I was like I wish I never met you are
people that I would just be cruel to say. Some guy I went to
college with. (laughing) – Oh yeah, no, that’s (laughing), talking about someone famous. – All right, I’ll take a shot. – Who’s the worst
standup comic in America? – The worst standup comic in America? – Or around the world. – I mean, morally worst,
let’s go back to Bill Cosby. (laughing) – You’re right, damn. Well played.
– Thank you. – Okay. – Question number six, when
John Oliver, your former boss, was a kid, what did he want to be? A, a professional bass player, B, a professional soccer player, C, the prime minister of the UK, or D, a veterinarian? – It’s professional soccer player, but he would say
professional football player. – You’re right. Do you have any good
behind-the-scenes stories about John Oliver? Does he rant in real life? Is that just how he is? – No, he’s great.
– Does he walk in a room and just rant? – No, he’s great, he’s very funny. He’s a great, nice boss. Early on when I was working for him, he called me G-Unit, because of my last name, Gondelman. So I was like, well then
I will have a rap name name for you as well, which
will be John Dre 3000. – That’s much better than G Unit.
– Yeah, no, no. – I think so. – Maybe, he assented to it, but I don’t know that
he was crazy about it. (laughing) – Talk about your new bosses. – Yeah! – Desus and Mero. – Desus.
– Desus. What the (beep) is wrong with me? The duo continually insist this baseball player is 100% Dominican, despite not a ton of proof. – I know this one too.
– You know this one? – I know this one off top. – Do you just wanna say it? – I could just say it. – I think you should.
– It’s Babe Ruth. – (beep) God, this is so sweet. Mm. Okay. My question is yeah, what
exactly do you do there? – The writing team kind
of works on the script for the show, like what they’re
gonna see in the prompter. There’s a lot of stuff
that necessitates writers. It’s a lot of bigger picture, making room for Desus
and Mero to improvise. – Sounds like they don’t really need ya. – Please don’t say that. (laughing) – You’re a–
– I really need this. – All right so you broke out
with a hilarious Seinfeld today Twitter account. Really love it. I wanna do a quick segment called, What’s the Deal with All these Shots? So, this is rapid fire Seinfeld trivia. The same rules apply. If you can get four answers
right in 20 seconds, you win the round. – That’s so fast! – All right, what fast food chicken chain kept Kramer up all night?
– Kenny Rogers Roasters. – Got that right. What is the name of the Scotch that “Doesn’t even make you
smell after drinking it”? – Oh, I don’t remember. – Starts with an H, okay you got it wrong. – What color is the bike
hanging in Jerry’s apartment? – Blue.
– No. – What’s the secret to
opening Elaine’s vault? – I don’t know.
– Oh my god. – What’s the name of Poppy’s restaurant? It’s Poppy’s. (laughing) – This is the secret about me is that I’m a big enjoyer of Seinfeld,
but not like a completist. – Wow.
– People always are like, hey Seinfeld, do you remember this one? And I’ll be like sure. But normally I’m not on camera answering questions with penalties. So, it’s easier.
– This is shocking. – I know, this is like
a Charlie Rose interview without the sexual harassment
goin’ on backstage. – Well, there’s still time. (laughing)
– Oh! That’s oh, thanks. (class taps table) – This is like Manischewitz. – Thank you. – Not a compliment. – I don’t know what that means. (laughing) – It’s the kosher wine. – Oh, that stuff. – How would you describe Nice Try? – It’s personal essays
and it’s just stories about being kind of a sweet kid, and trying to figure out
how to be a good person. So, it’s stories about trying and failing to do drugs in a bathroom in Williamsburg. – What kind of drugs? – Well, it was not drugs at all, but we thought it was molly. – Oh. (laughing) – You know what, no spoils. – It’s in the book. Yeah, you gotta read the book. – So, I wanna talk about
one of the biggest blunders in world history. (laughing) Has nothing to do with you. – You’re like, World War II, what a goof. – In 1788, which country’s
military drank so much on the eve before battle,
that they accidentally ended up fighting each
other, killing 10,000 of their own troops
before any enemy arrived, thus defeating themselves
before the war even started? A, France, B, Austria, C, Canada, D, Russia. – I wanna say Russia. That’s some kind of
ingrained prejudice I have. It’s not based in any knowledge, and I’m not gonna not say it. So, Russia. – No, it’s Austria. – Austria, really? All right, so this is mine? – Ya. What was the biggest mistake of your life? Military or otherwise and
what did you learn from it? – When someone was mean
to me that I was dating, I was like, great. – Oh. (laughing) – That’s what it’s all about. – Like a sex thing? – Not a sex thing, that’s a different, no, that’s a different kettle of fish. Just like mean conversationally. – Oh, that’s not cool. That’s not sexy.
– No, it’s not sexy! For someone to be like, “I don’t know, I don’t,
I guess we can hang out.” And it would be like oh, get ready for me to win you over by being too much and annoying, and making you like me less. – Yeah. I’ve been there too. Well, what did you learn from that? – Well, I am a married person, and my wife–
– Congrats. – Thank you and my wife is
lovely and is very nice to me. And I like that a lot. (laughing) – Number 10. What was the brand name
of the penis-numbing spray you notably tested out in a
2013 New York article. You know the answer to this one? – I remember this, it starts with a P. – You’re right.
– Yeah? – But can I just read through, just– – Sure.
– To do the farce. – I wanna hear the fake ones. – Promescent, Endurascent, Fromnescent or No Explode. (laughing) – It’s Promescent. – It’s Promescent. Last shot, that was it, question 10. We got through.
– We did it. – Do you still use Promescent? – No.
– Okay. – I barely… (laughing) – All right, this is ridiculous, okay. – Yeah, it’s ridiculous. – Cheers. Mm. That was it, we got through it. – L’Chaim. – What? – Nothin’.
– Oh, okay. (laughing) – We did it, we blazed through these. – Would you sign our bar? – Yeah, of course. I will write my name. – This was fun. – This was fun, we had some laughs. – We learned a little bit. – We did. – I cried a little. I don’t think you noticed. – Mm hm.
– You saw that? – Oh, yeah. – I thought it was beautiful. – I had one– – One tear.
– Like one down. – Yeah, one tear. Like Sylvester Stallone
remembering a friend that died. (laughing) – Cheers.
– Cheers. – And now Buzzed
Bartending with Wil Fulton. – And this is how you make today’s drink, the Gond with the Wind, designed by Reclamation
Bar’s, Garrin Ferry. Two ounces of rye, (water splashing) or a little more if you’re feelin’ frisky. (cup taps) .5 ounces of blueberry liqueur. (liqueur splashes) And five ounces of lemon juice. (juice pours) And .25 ounces of simple
syrup of your choosing. (liquid pours) Shake thoroughly. (liquid shaking) (liquid pouring) (bottle taps) – Ah. (sighs) (smacks lips) It’s good. Thank you for watching “Shoot Your Shot.” Subscribe to Thrillist’s
YouTube channel, all right? I will buy one shot.
– Like and subscribe. – Do all of that.
– If you just subscribe, I will find you. – And buy his book, “Nice Try.” – Yeah, buy “Nice Try.” Do that before you even
like and subscribe. Honestly, I’ll throw them
under the bus in a second for book sales.

4 thoughts on “Comedian and Desus & Mero Writer Josh Gondelman Takes Shots, Talks Working for John Oliver || SYS

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