The lack of surprises at this year's Academy Awards didn't stop the 170 dinner guests at V.F.'s 11th annual awards-night bash at Mortons, in West Hollywood, from making a few friendly bets. Then again, the hobbits hadn't begun to collect their 11 Oscars when $20 bills started flying across the Emerald-rose centerpieces. (Hilary Swank won her table's pool but had no place in her skintight, vintage Valentino gown to stuff the cash.) Watching the broadcast on one of 11 giant screens, General Tommy Franks laughed heartily at host Billy Crystal's wisecracks about the Middle East, as luminaries of every stripe—among them Sidney Poitier, Nan Kempner, Anjelica Huston, Jon Robin Baitz, Tom Ford, Sumner Redstone, Donna Karan, Anderson Cooper, Jay Leno, and Sherry Lansing—dined on a meal created by Lorenzo Roman of Mortons and guest chef Geoffrey Zakarian of Town. Just 15 minutes after presenting a tribute to the late Bob Hope, Tom Hanks arrived to join wife Rita Wilson and friends Martin Short and Steve Martin. Dennis Hopper and Harvey Keitel cheered the loudest when Sean Penn won for best actor, and Larry David and his wife, Laurie, sat with V.F.'s Graydon Carter, who avidly employed the custom-designed pink-and-green cigarette lighters that were given out as party favors.

As soon as the awards ceremony ended, the tables were whisked away to make room for some 1,200 illustrious guests, who passed a 30-foot VANITY FAIR topiary en route to the social swirl. Sean Penn, family in tow, held court with Mickey Rooney and a queue of A-list well-wishers. Renee Zellweger paired up with boyfriend Jack White, and Nicole Kidman saved seats for Naomi Watts, Heath Ledger, and their Australian brigade. Oscar winners Tim Robbins and Charlize Theron appeared with their respective partners, Susan Sarandon and Stuart Townsend; OutKast's Andre 3000 met Joni Mitchell, Elvis Costello, and Costello's wife, Diana Krall; and best screenwriter Sofia Coppola toasted success with her dad, Francis, and her cousin Nicolas Cage. It was so much fun that even the In-N-Out Burger truck stayed late, serving cheeseburgers to Hollywood's finest until the wee hours.