Jeff Ross Talks Season Two’s Roast Battle Finale From the Set of HBO’s Crashing

In Season Two, HBO’s Crashing has moved way past ’ failed marriage and open mic appearances. Throughout this season we’ve watched Pete make his way through the alt rooms of New York City, attempt to hang on to his relationship with , rub elbows with some of the best in the business, and experiment with some different types of comedy, including pandering to an audience for approval.  We’ve also watched him awkwardly navigate a new relationship with Ali, making many mistakes, but still finding a way to keep things moving forward. Seasons two’s twin arcs come literally crashing together in the season finale, as Pete attempts a style of comedy completely foreign to him- Roast Battle and puts his relationship to what may be the ultimate test. Can Pete and Ali’s weird relationship survive a Roast Battle?

I visited the set the day the season finale was filmed at Gotham Comedy Club in New York City, and if you’re a comedy fan, it’s hard to imagine a day of filming more fun to observe.  Regulars from the New York comedy scene and LA comics were in the room, on stage, milling about the set for the taping, with many of them participating on stage in the Roast Battle. The jokes are brutal and funny, with great improv material from the Roast Battle judges Beth Stelling, Jeff Ross, and Artie Lange.  Jokes were being punched up and rewritten on the fly with a team of writers printing out new sides throughout, and every battle was a killer.  Tony Hinchcliffe takes on Holmes in this episode, and his brutal writing was used not only to eviscerate Pete, but also to skewer himself.

I got to sit down for a few minutes with the undisputed King of the Roast, , to talk about the episode, and the state of roast comedy in general. “Its just a world-wide movement,” he explained talking about the roast phenomenon. Its gone to other countries now.” Ross says he thinks its just human nature to love to see your friends or big-shots taken down a notch. “I think its therapeutic for people to laugh at themselves. Whether its Justin Bieber on TV or the guy who came on stage at my show at Radio City in a wheelchair and never been roasted. Never even been talked to that way.  He was laughing so hard I thought I was going to fall down and be crippled by his jokes myself. So it’s a very therapeutic thing. I think its harsh comedy for hard times.  And its working.”

The idea to incorporate Roast Battle into the HBO series came from the Crashing team. Pete Holmes called him up  about it, adn then Judd followed up to find out Ross’ availability.  “And next thing I know my friends started calling saying ‘Hey, I’ll see you in New York. Hey, I’ll see you in New York. Hey, I’ll see you in New York! It turns out like thirty comedians are in one episode and its just like our own little comedy festival right here in this league. It was nice having all the other roast battle family here. It was really special and it’s a great show so it’s a great hook for Roast Battle too.”

It’s a risky prospect to put a show you’ve created in someone else’s hands, and Ross knew that.  “You always have a little bit of worry, like, are they going to have actors…when you do these sorts of things normally, are you going to have actors playing comedians or are they going to do it authentically,” he said.  But the Crashing team did not let Ross or Battle fans down. The competition series, which aired for two seasons on Comedy Central, was recreated faithfully, with series creator Brian Moses hosting, Jeff Ross of course presiding over the judges table, and even The Wave – Jeremiah Watkins, Willie Hunter and Jamar Neighbors- recreating their role as live-action whammies.  “Here we are, in New york with all the real comics playing themselves its kind of perfect,” Ross said. “Its like we’re all acting as ourselves doing Roast Battle it’s a little bit of like looking in a mirror in a fun house.”  One small difference- you’ll notice the chants changed.

The Crashing writers did more than just capture the window dressing, the battles themselves are both fun and funny, Ross noted. And they capture one more detail of the real thing– they hurt.  Just like in the real Roast Battle, some of the hits cut close to the bone, even for the actors.  “Pete has never done a Roast Battle so watching him– and he can even do one as an actor– he’s still hurt he said. Even though it’s a fictitious roast battle the jokes still sting ’cause the jokes are real.” And for others, the sting of losing a battle, even when its a loss written into the script, can hurt. “Tony [Hinchcliff] has been a great sport…but I can see it in his eyes, I love Tony. It definitely hurt him to lose even a fake battle.”

The outcomes might have been pre-written, but the judging, at least for Ross, was not. “I’m doing it like it’s a real battle. Their telling me what they’d like the outcome to be, because its pulling the story, pushing the story forward.  Within that, I’m trying to do it as realistically as possible.  I know all the battlers so I can give them encouragement and I can make fun of them in a personal way, which is fun. So it’s so natural for me that I’m not even sure what I’m doing out there.”

And the audience may have been hired extras, but thanks to the way the show was produced, Ross said many of the actors became Roast Battle fans.  To acclimate them and keep the laughs authentic, Pete went on stage at 7am before shooting becan to explain to the extras how the show worked, and Ross went up to make fun of some of them to set the tone, something Ross said was great producing.  “I think honestly, I think some people will see this episode on HBO and go, that would be a real…a real comedy show. And then they’re going to find out now that it is real comedy show.”

That authentic portrayal of the stand up comedy scene in New York has been a hallmark of season two in particular, and the series in general. [The show] is very honest. We’re getting real nightclub, comedy club laughs in a scripted show. It’s kind of a perfect hybrid of stand-up, roasting and acting. And comics– as real fans know– are good actors.”

The episode airs this Sunday, winding up a really strong season. With dozens of comedy guest stars including Yamaneika, Aparna Nancherla, Beth Stelling, Damien Lemon, Mike Lawrence, Tony Hinchcliffe and so many more, don’t miss the season finale of Crashing.

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