Seinfeld Roasts Tommy Chong, and Other Weird Things That Happened on the Playboy Channel

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A warning before we get into this: this installment is going to feel a little bit like a trip to an alternate dimension. A dimension in which the Playboy Channel aired things without boobs. Where Tommy Chong is a name big enough to be on a televised roast. Where Richard Belzer isn’t a network TV detective. Where Jerry Seinfeld is big, but not Seinfeld big, and yes, he has to stand at the dais and say mean things about a fellow comedian. Welcome to the world of 1986’s Playboy Comedy Roast of Tommy Chong, which aired exclusively on the Playboy Channel, and was a really weird time for everybody, including the audience.

To begin, let’s run through the lineup. First and foremost, there’s Tommy Chong, the guest of honor, best known as half of the original stoner comedy duo Cheech and Chong. Our MC for the evening is David Steinberg, currently the host of Inside Comedy on Showtime, and frequent guest of Johnny Carson’s Tonight Show. In addition to Seinfeld and The Belz, our roasters include Slappy White, a comedian of the old school, who came up on the so called Chitlin’ circuit of standup in the 50s and 60s, working with Redd Foxx before becoming a Friar’s Club roast superstar. Also at the head table are Mack and Jamie, a comedy team who at the time were the stars of their own syndicated comedy show Comedy Break with Mack & Jamie. Dick Shawn, who played the actor who played Hitler in the original film version of The Producers is there, breaking out of his traditional stuffy demeanor. And finally there’s Marsha Warfield, who is probably best known as the bailiff from Night Court, who David Steinberg touts as the very first woman on the dais of a roast. “Because of the presence of a woman, we’ll be a little more contained than usual tonight,” he says, beginning his joke. “Fuckin’ well better be,” she interrupts, ending it for him.

But let’s begin with Jerry, who appears at the midpoint of the evening, because if you’re like me, you’re probably curious how Seinfeld handles himself at a roast. If you were to ask me to come up with one Seinfeld routine that is about a specific person or at the expense of someone, rather than be about the human condition in a larger sense, I would be hard pressed to name one, with the exception of his dad controlling the thermostat. Jerry begins his set by making fun of the type of casino/hotel he’s performing in, saying, “The amazing thing to me about the casino hotel is that they manage to locate everything in the hotel across the casino. You go out there, where’s the elevator? Where’s the coffee shop? Across the casino. Every trip costs you $12 in quarters.” It’s the quintessential Seinfeld joke, before the world really knew what that was.

Then Jerry moves over to Tommy. He begins with a story about the first time he ever saw him, back when he was in college, and Tommy did a routine about two dogs that, in Jerry’s own words, which he clearly feels a little outside his comfort zone saying, “take a dump and talk to each other.” While watching him perform, Jerry says that he thought to himself “anyone can do better than that.” He then zooms out a little bit and talks about Cheech and Chong’s film career. “You know what I like about their movies? The suspense. Will there be car trouble? Will there be a Mexican accent? I like the movies… They don’t play at the specially selected theaters. They play at the theaters near you.” And from that line, he transitions away from roasting Chong and into regular Seinfeld material. “You get ripped off on candy there. It’s in that glass case. It’s like a jewelry case…” He goes from that chunk, to a run about the TV show That’s Incredible, to a bit about wearing tuxedos (which contains the great line: “If you’ve ever rented one, it’s fun wearing clothes that 80 different high school kids have worn on the most exciting night their glands could ever dream of.”) It’s the perfect method for him: do a joke at Tommy’s expense, and then transition as quickly as possible into the comfort zone of the material. Comedy Central’s run of roasts has made the expectation that a comedian must be as mean as humanly possible while up on stage, but clearly this was a different time, and so there was room for all kinds of comedy at the Playboy Comedy Roast.

Let’s take a look at some of the other highlights/weird things that happened this night. Slappy White starts the evening, and he represents the era of comedy that he began in. Rather than make specific jokes about Tommy Chong, he mostly tells Chinese jokes, including “Confusus say that Chinese invented the toilet seat but America put a hole in it,” which I am 100% cool with not understanding.

Up next is Richard Belzer who is introduced as a “cult comedian.” Belzer’s approach to the roast felt the most contemporary to me, first focusing on the rest of the dais, taking each of them down, and then turning his sights on Chong. However, he couched the entire thing through the framing device of a conversation with a friend. “When I told my friend I was doing a show for the Playboy Channel he asked me ‘what are you doing up there with those guys of such talent?’” Whenever a joke got a huge reaction from the crowd as being a particularly harsh burn, he simply rocked on his heels and agreed with them, hiding behind the fact that “his friend” said it; not him. Belzer did a great job of marrying his offbeat personae with the roast mentality and produces a very fun set.

Marsha Warfield’s set was very dry, and she managed to squeeze a lot of laughs from slow pauses and looks to the audience. I don’t know how often this female African-American comedian was compared to Jack Benny, but they share a lot of similarities in their sense of timing. By simply saying it flatly and without emotion, she manages to get a huge laugh out of her first sentence: “I’m especially thrilled to be here,” which was her second biggest laugh, right behind, “So now we get to the important question: who the fuck is Cheech? Would you go to a concert to see just Hall?”

Mack and Jamie do a short set, breaking out of their clean personas, telling jokes about performing oral sex on Don Ho. Following them, Ray J. Johnson Jr. makes a surprise appearance as Cheech Marin. That last time this character appeared in From the Archives, I referenced Krusty the Klown from The Simpsons episode “Krusty Gets Kancelled” in which he says that the only bad show he ever did was the one that Johnson co-hosted. “‘You can call me Ray, or you can call me J.’ That thing was funny for about three seconds.” I stand by that reference. Dick Shawn takes the dais, takes a stoic look to the crowd and then spits fake vomit all over the podium (it’s glass too, really allowing it to make an impact). I’m not going to say it wasn’t a funny move, but I’m also not going to say it deserves the full minute of laughter and applause it receives, though I am a fan of his follow-up line: “I’m sorry. It just seemed like the right thing to do.”

Finally, Tommy Chong takes the podium. He stays true to his persona and immediately states that he did not plan anything to say. “This is weird, man. I was sitting there, enjoying the show like you guys, and then I had to start thinking about what I was going to say.” Tommy stays very sincere, and is thankful for the attention and kind words he’s received this night, before sitting down and ending the show.

Despite the fact that this roast aired on premium cable, specifically on a channel that primarily broadcasted pornography, it feels rather toothless by today’s standards. Many of the comedians didn’t seem to roast Chong. Those that did often did so by inserting Tommy into traditional street jokes, rather than citing actual events and elements of his career. Is this just a matter of the “meanness” evolving, or was this just not the right pairing of target and comedians? Whatever the cause, it’s safe to say that there was no part of this special that did not feel off to me while watching it, and I’m glad it’s over.

Ramsey Ess is a freelance writer for television, podcaster and a guy on Twitter. His webseries “Ramsey Has a Time Machine” has a very self-explanatory title.

Seinfeld Roasts Tommy Chong, and Other Weird Things […]