Wednesday nights became theme nights at the Viper Room, called Mr. Moo’s Adventure, named after Johnny Depp’s dog. One Wednesday might be “Women in Prison” night, with the V.I.P. booths turned into prison cells; another might find the club converted into an airplane; another would have the black walls covered with aluminum foil. These elaborate evenings were money losers but fun for the club staff.

The Viper Room hosted two episodes of its version of The Dating Game; for one of them, bar back Richmond Arquette recruited his younger brother, actor David Arquette (Scream) to be the bachelor. Richmond wrote some questions for his brother to read to his romantic prospects, but when David attempted the first one, he laughed so hard, he couldn’t get the words out. The question was: “I like to masturbate for hours on end until I’m in danger of dying from dehydration. What do you like to do in your spare time?”

Another night, the bachelor was actor Norman Reedus (now most famous for The Walking Dead). “They sort of set him up,” Richmond Arquette remembered. “One of the bachelorettes was this Mexican tranny. They gave her the best answers, and he picked her. When Reedus’s choice was revealed, “even though it was all in jest, you could see her vulnerability. He did this beautiful thing: he kissed her, said, ‘I’m so happy,’ and was really gracious about it. I always liked him for that.”

After the emotional wringer of filming Gus Van Sant’s My Own Private Idaho, “I just did not feel like barreling through someone’s psychosis,” River said. He opted for a low-stress money gig: Sneakers. As one actor in the film said of the title, “It sounded like a bad teen comedy about a hapless junior-high basketball team that is saved when they recruit a girl point guard who’s a great shot.”

The movie was actually a heist caper centered on a band of professional computer hackers and security consultants; the N.S.A. dragoons them into stealing a black box that is the ultimate code-breaking tool. Director Phil Alden Robinson (Field of Dreams) assembled an absurdly star-studded cast: Robert Redford, Sidney Poitier, Dan Aykroyd, and Ben Kingsley, not to mention Mary McDonnell, David Strathairn, and James Earl Jones. A hugely classy ensemble—but the studio wanted to make sure that there was also some youth appeal and pushed for River.

On the set, River quickly bonded with Aykroyd (another actor who really just wanted to rock). The two of them would gaze awestruck at Redford and Poitier, River said. “We’d think, ‘These guys are like national monuments, like the pyramids.’ And that poses the question, ‘But what are we?’ Well, I guess we’re sand crabs or scabs or something less dignified.”

Aykroyd and River had a host of running jokes; they dubbed the catering truck the Roach Coach, which evolved into calling each other Mr. Woach and Mrs. Woach. River would pinch the fat on Aykroyd’s waist or blow on his bald spot. “Just complete, absolute, total irreverence,” Aykroyd said. “And he could get away with it.”

The first day of shooting, Robinson thought River was fine—but when he saw him in dailies, he was much more impressed. “He makes very quirky choices that really come alive on film,” the director said.

The quirkiest choice of all comes during a montage at a party, where most of the cast takes turns dancing with Mary McDonnell while Aretha Franklin’s “Chain of Fools” plays. Poitier is all stiff reserve, while Aykroyd proves to be a surprisingly accomplished swing dancer. And then River flails around like a punk moshing at a Germs concert, kneecaps bobbing and arms waving. It’s the most visually arresting seven seconds in the movie.