Stewart took over The Daily Show in 1999, but in 1993 he was providing commentary on a basketball game involving Flavor Flav, Mark Jackson, Danny Baldwin, Kareem Abdul-Jabbar (coach) and many others. If you’re not familiar with “Rock N’ Jock,” here’s a brief summary, via Wikipedia.

What the summary doesn’t tell you is just how crazy the games were. In the episode (third of the series) that features Stewart as an announcer, the first 25-point basket was introduced. Yes, a basket that is worth 25 points. This basket is placed high above the original rim, making it difficult to score.

There were also spots on the floor, near the 3-point line, that counted for 10 points. There was also a penalty box for players who acted up, and players were allowed to dunk their free throws. Really, there were no rules other than to have fun and try to win.

In the game Stewart announced, there was plenty for him to comment on. If you want to avoid spoilers, just watch the video above. But in case you don’t have an hour to watch the footage, I’ll briefly break down the game and Stewart’s commentary.

The teams facing each other were the Bricklayers and the Violators. The teams were made up equally of celebs and athletes, so no one team is at a clear advantage. Some of the shenanigans that took place included a benches-clearing brawl (a playful one), Flavor Flav blocking shots with a hockey stick and talking to players while they’re on the court. There was also a dunk contest and a 3-point contest, but these were severely underwhelming.

As for Stewart, he handled every situation like a pro. He came up with funny lines like, “Michael Rapaport is so white” and “do you think Danny Baldwin has ever played basketball?” His job was to play alongside Albert, who did most of the play-by-play work.

Albert spoke with Suns.com about his experience working with Stewart, and was amazed by how well he did.

“Jon Stewart? Whatever happened to him? I guess he peaked with MTV Rock N’ Jock and just couldn’t get a break after that!” Albert said jokingly. “Jon was an up-and-coming comedian at the time but one of those guys who had the ‘it’ factor. You knew he was destined for something special. But of greater significance to me was his humility and the way he carried himself. He was a true sports fan, very respectful of yours truly as a play-by-play announcer and seemed genuinely thrilled to be my color commentator. For a situation that might have been somewhat foreign to him, he handled it like a pro, like he’d been doing it for years … knowing exactly when I was supposed to speak as well as when it was his turn to speak. And when he spoke, he was usually witty and funny.”

Stewart was likely selected since he had a show on MTV that started in 1993 called, “The Jon Stewart Show.” He stayed with the “Rock N’ Jock” show for a while, including an appearance in the 1995 softball game. He’s pictured here with Dan Cortese and George Clooney.

Cortese talked about this image in an oral history of the MTV show with Complex.

“Rande Gerber, who is married to Cindy Crawford and is doing a tequila with George Clooney, sent me this picture about two weeks ago,” he said at the time. “It’s Clooney, Jon Stewart, and me looking like Space Ghost with those Oakley shades and that hat. I said, ‘Yeah, two out of three ain’t bad. I guess George and Jon did all right.’ That said, I did hit two home runs and walked out with the MVP that day.”

Stewart ended up leaving MTV and “Rock N’ Jock,” and he moved on to better things. Over the past 16 years he provided entertainment to millions on Comedy Central’s “The Daily Show.” His final days are upon us now, but he’ll leave a lasting legacy. We’re thankful his career didn’t end as an announcer providing commentary on Flavor Flav playing basketball.