Talking Gambling With Comics: Clayton Fletcher

Talking Gambling With Comics: Clayton Fletcher

Talking Gambling With Comics: Clayton FletcherLike many comedians, Clayton Fletcher leads a double life. He splits his time between the stage, both on the road and in his home base of New York City, and a day job. But unlike most comics, his day job is playing poker.

Originally hailing from Maryland, where his mother was a professional poker player and his father was a jazz musician, Clayton has played in cash games and tournaments around the U.S. and the world throughout the last decade. During the poker boom he once won three satellites to big tourneys – the WSOP Main Event, the Aussie Millions, and a charity tournament at the Playboy Mansion in L.A. – in a single year. That trip to the Aussie Millions led in roundabout fashion to a headlining gig at The Last Laugh in Melbourne. That experience, along with his time spent at the table with veteran comedian Kevin Pollak during the 2012 WSOP Main Event, later led to a short feature about his double life in Bluff Magazine.

A true comic, Clayton spoke with me earlier this week from the road.

JK: You’re an expert in both poker and comedy. Who’s the funniest poker pro you’ve played with?

CF: Definitely Mike “Timex” McDonald. That guy’s hilarious. We played in one of the bracelet events, I think it may have been one of the $1500s, and he had made a bet with one of his friends that if either one of them won a bracelet that the other one would have to wear that bracelet to all the tournaments for the rest of the World Series and have to answer the question, “Hey, where did you win that bracelet?” “Well actually, I didn’t win it. My friend, to whom I lost the bet, won it. And he beat me because he’s a better human being than I am.” And his friend – I wish I could remember who it was – won one.

They had this whole speech they had to give to anyone who asked about the bracelet. And all kinds of people know Mike McDonald so they’re coming up to him every 10 minutes, asking what event he won, and he had to give the whole spiel probably 100 times throughout the day. At the same time we were laughing and carrying on because he and his friends throughout the summer, whatever house he was living in, they were having sort of an Olympics alongside the WSOP to determine who was the most awesome person. So you’d have anything from arm wrestling to bowling to who could make the best milkshake. He was describing all these events and we were brainstorming together trying to come up with more events to include in their Olympics. I’d never met him but I’d heard he was a really funny guy. I liked playing with Timex a lot. He’s a really good player but he also knows how to have fun at the table.

JK: What is the toughest table you’ve ever had to play in one of these tournaments?

CF: That’s a tough one. In the Main Event, the first year they did the November Nine, I had a brutal table. Matt Jarvis, who made the November Nine, was there. He was a really tough player. It wasn’t a list of “who’s who” – not Dwan and Ivey and Mizrachi – just a bunch of online guys who were really, really tough.

I was on a podcast recently called Thinking Poker with Andrew Brokos. We were talking through a hand I played at a tough table in the LAPC, a $1000 buy-in. At my table I had Owen Crowe, Jeff Madsen, Jonathan Little, and two unknown guys and me. It was supposed to be a full-ring table but I got there early and most people came late. So we played five- or six-handed for a long time, and I had those guys to contend with. That was pretty tough. I wasn’t making too many jokes that day. I was just trying to survive!

(Those players) just don’t make mistakes. It’s usually easy for me to figure out to exploit a player’s tendencies, but what great players do is constantly adjust and make changes to their game. They always kept me guessing. I feel like any time the opponent is guessing, you are in a position of strength. So I thought at that table that I was the one doing most of the guesswork. I was outclassed for sure. Kind of put me back on my heels a bit. And as a result I tried to come up with a strategy against such a strong lineup.

I tried to figure what they thought about me at that point. I didn’t think any of them recognized me, though I played with Jeff Madsen at the final table of that Playboy tournament, which was a charity event – I won third place in that event. The proceeds went to charity but there were prizes for the final table. I got the coolest prize for third place, a Fender guitar that had a Playboy emblem on it and was autographed by four Playmates of the Year. So that was pretty sweet – probably worth more to me than the money with.

JK: And that gives you something to crawl up in bed with at night when a set doesn’t go well, right?

CF: (laughing) Yeah! “Oh, Sara Underwood, I love you!”

JK: You’re originally from Maryland. Have you been to play at Maryland Live yet?

CF: Yeah. They had a big tournament there in March. $500 buy-in, and I think they guaranteed $500,000 – it was a great tournament and they did a great job running it. The rake wasn’t too high, which is a big problem in a lot of tournaments nowadays. It was a really great event and I was glad I could go down, visit my family, and play some high-stakes poker. Unfortunately I didn’t cash, but I’m definitely going to play in that event next year. It’s a nice new casino.

It should be interesting because this summer they’re opening a new Horseshoe right down by the stadium in Baltimore. It’ll be interesting to see whether those two casinos are able to co-exist and thrive. Right now there are two other casinos in Maryland but they’re small compared with Maryland Live. I think some of the people who drive halfway to Washington are going to say, “I’m going to stay local, play a few hours of poker, catch an Orioles game.” I think there’s a point where things get saturated, but hopefully that won’t be the point.

I was talking with my friend about a week ago about what’s going on in Atlantic City. All the casinos in and near Philadelphia opened up, and then one in Delaware, and there’s just so much more competition for the Atlantic City casinos. That used to be the only gambling for miles! That place is really trying hard to persevere, but at some point you do reach a saturation level. A couple of places there have closed or gone into bankruptcy. I remember Atlantic City when it was second only to Vegas.

JK: Back during the poker boom they used to show the US Poker Championships from the Taj —

CF: Yeah, the Taj! I remember, we all watched that.

JK: They played it up like it was a really big deal. And then a few years into the boom they stopped showing it on ESPN. The first time I went there I walked in and thought, “No wonder they stopped showing it on TV, this place is a dump.” You see the chandelier over the escalators that’s in the famous scene in Rounders, but you had to pass homeless guys sleeping on benches to get to it.

CF: (laughing) Yeah, it’s not pretty. It’s funny because my aunt plays poker, and she said, “I remember when Taj Mahal just opened and all the waitresses were beautiful and the place was sexy and had panache.” And I said, “As far as those waitresses go, it’s the same girls still working there now!”

JK: They’ve been on shift since the beginning of time.

CF: Yeah, since the very beginning! They don’t have the same bodies they used to in those skimpy little outfits.

JK: Do you get to play much poker with others in the comedy business comics, in home games or on the road?

CF: Yeah. I actually made a great connection through poker and comedy. I used to have a manager named Marty Fischer – may he rest in peace – he invited me to a poker game one time many years ago on Super Bowl Sunday. He said, “Hey, I know you play some poker and I want to take you to this private game. It’s in a suite in a hotel. There are going to be some well-known comedians there and some comedy people I want to introduce you to.”

He was trying to help me make connections. This was when I was just starting to get known in the comedy world, maybe 10 years ago. We ended up playing $100 buy-in, two-table sit and go’s all night. And I was by far the best player in the room! I don’t want to say who the other comedians were, because they might not appreciate me mentioning their names, but there were definitely some guys in the room that we’ve all seen on TV a lot, let’s put it that way.

But one of the guys who was in the room was Al Martin, who owned the Broadway Comedy Club in Manhattan. There were 16 or 17 players and the two of us got down to heads-up. I turned to my manager Marty and asked, “If I don’t let this guy win, is that a bad career move?” (laughing) He owns this famous comedy club, and I don’t want to get on his bad side over a game of poker! We all had a laugh. And then Al, the owner of the club, said, “I tell you what, if you let me win, that’s the bad career move.”

So I ended up beating him. He said, “If you’re half as funny as you are good at poker, you have a bright future in both. I’d like to work with you – maybe you can teach me some of the tricks of the trade in poker, and in exchange I can start booking you at my club and I’ll take a look at your set.” So basically, the way you’ve heard legendary stories of old-school business deals getting done on the golf course – that was where the networking took place – I think now I think business gets done at the poker tables.

I’m still friends with this man, I have a show at his comedy club, The Clayton Fletcher Show, and I have basically carte blanche to perform there anytime I want. So I started teaching this guy to play poker all these years ago, and as fate would have it, after a few lessons with me, he won the first tournament he played. So that just made me look like a genius.

JK: That’s the best possible thing that could have happened!

CF: Yeah! He said, “You’re the best teacher in the world!” I mean, we all know that luck had a lot to do with that. Any time you win a tournament, luck is a major factor. But it made me look and feel good. So that was kind of the way that I parlayed my love of poker into a business relationship in my other double life/career that I have going. We still travel together. We’ll go to Atlantic City, we’ll go to Florida and play in some of the big tournaments there, we’ve been to Vegas. He’s one of my best friends and it all started with my manager thinking of me when he got invited to that poker game. And the rest is history.

You know, if I’d sat there with my headphones on, my sweatshirt wrapped over my head, I don’t think I could’ve made the friends I made that day. Who knows what effect that might have not had on my career? I think when you’re talking to people, engaging with them, laughing together, you’re more in touch with the game, you know?

I’m in Cleveland right now, and last night I played at the Horseshoe here. These guys were all on their tablets, their cellphones, just multitasking, not really paying attention to the game. And as a result I could identify mistakes that basically all of them were making. I don’t know – I understand poker can be boring, especially when you’re card-dead for three hours straight, just folding, but I try not to be on my phone and texting and Googling and sending emails and everything else besides paying attention to the game, because otherwise you don’t get to know some of your opponents. And some of them might end up being your best friends.

JK: So if you could put together a six-handed table of comics that you know to play a night of high-stakes poker, who would you want at the table?

CF: Amy Schumer. She’s a friend of mine and she’s hilarious and she’s pretty good at poker. She’s fun to play with and always, always funny.

There’s a comic you might not know named Rich Aronovitch. I’ve played poker with him before. He’s really funny and he loves to have a great time. And he doesn’t care if he’s winning or losing, he’s just a fun guy to be around.

Dean Edwards, he was on Saturday Night Live for a while and has done a lot of stuff on Comedy Central. Great guy, really funny, I doubt he’s very good at poker but I’d want to invite him anyway!

JK: You have to have a few soft seats at the table, right?

CF: Yeah, we don’t want this thing to be too tough! Let’s see – Jessica Kirson. Oh, I’d love to play poker with Jessica Kirson. That would be a lot of fun. She’s done The Tonight Show a few times, she’s a great comic and a good friend of mine and she always brings the party wherever she goes.

And let’s get John Pinette in there. He’s dead and gone, passed away recently – he wasn’t necessarily a comic that everyone knows, but he was just one of the most fun guys to be around. I miss him a lot. He was a good friend of mine. You said players I know, but you didn’t say they all have to be alive! (laughing)

If you get the right mix of people together, you’re going to have a good time. I think a lot of comedians wouldn’t be comfortable playing high stakes poker because a lot of comedians, even with the successful ones —

JK: —are broke?

CF: Well, they might not be now, but they definitely remember a time when they were. Even comedians you see regularly on TV, a lot of them are shocked when I tell them that I’ve been able to maintain a bankroll while having a poker career and a comedy career. Because in the comedy world it can be that one day you’re doing a gig someplace for $20,000 and the next day you’re out of work for a month. It’s almost like tournaments in that you don’t win every time!

JK: You’re playing the Las Vegas Hilton in May. How is playing a comedy show in Las Vegas like playing poker?

CF: The basic thing is that the people that you’re dealing with are from all over the world, and they all have their own opinions about what’s good and bad. Your job is to read them and figure out what’s working and what isn’t and then make adjustments accordingly. To me that’s the essence of both poker and comedy. It’s about making adjustments in the moment, based on the verbal or non-verbal feedback that you’re receiving from your opponents or your audience, whatever the case may be. Being able to make those adjustments is really what it comes down to.

I enjoy both equally. I’ll probably never stop doing either one. Apparently I’m pretty good at both of them, so lucky me! I’ve put a tremendous amount of work and effort into both of my careers, and ultimately I hope to someday be able to combine them. I could see myself doing on-camera for a poker TV show, or maybe doing some sort of commentary or hosting where I can take these two worlds that I’ve submerged myself into for all these years and somehow putting them together in a venture that would allow me to exploit all my talents.

JK: Back before UIGEA, during the boom, those gigs were everywhere. I think if online comes back in full force they will be again, too.

CF: Yeah. And I’m a lot better known now than I was back during the boom, so hopefully the stars will align once again and this time I can be ready.

JK: And even if you’re not ready, you can get some good material.

CF: (laughing) That’s right. Failure is funnier than success anyhow!

Follow Clayton Fletcher on Twitter at @claytoncomic, as well as on YouTube and Facebook.