And he is generous, too, with strangers. In a touching tribute to his marriage, he gathered his friends at Irving Plaza for a twenty-fifth-wedding-anniversary party last February. Before the evening's headlining act, Willie Nelson, took the stage, Sillerman stepped under the bright lights and presented Laura with $100 million to launch the Tomorrow Foundation, a charity to be run by her. "Bob is usually Mr. Entertainment, the Milton Berle of my life," says Irwin Kruger, a McDonald's franchiser who has known Sillerman for nearly 40 years. "Here he was giving this lovely speech, saying, 'We've been so lucky, and we're not just giving back but thanking everybody.' "
"I think Bob, more than anything, has changed from somebody who was looking outward and is now able to look inward," says Laura, who notes that the birth of their daughter, late in their lives, has "mellowed" her husband. "Bob has become extremely conscious of wanting other people to get the first helping, of attention, joy, even credit. That's a good thing to know about yourself, that there's enough to go around."
Tom Petty is wearing a grungy green army jacket, wandering around backstage with a willowy blonde young enough to be up past her bedtime. It's a hot night. Sillerman is making believe it's no big deal, but he wants to meet Petty. He's circled the field at Southampton College three times, even changing out of his Petty T-shirt because that might not look cool. His buttery cowboy boots are losing their shine in the dust. And the roadie patch on his faded-to-white Levis isn't getting him anywhere.
He flips open a Motorola cell phone and tells the housekeeping staff to prepare a room in case Petty wants to stay the night. Snapping the phone shut, he sidesteps a caterer lugging buckets of chilled Thai calamari and exits the VIP tent onto the field. An eardrum-rattling organ is punching out the hypnotic riffs of Petty's "You Got Lucky," testing the sound system of his Arabian-themed stage set. "Isn't this amazing?" says Sillerman, gazing -- like a flower child finally seeing Woodstock -- at the velvet draperies and rococo set. "This place was absolutely empty this morning. I watched them raise the roof."
Although it's a benefit, this event could serve as the blueprint for Sillerman's grand plan. The show is heavily sponsored. Hundreds of Revlon gift bags line the entrance to the VIP tents, packed with Iced Mocha nail polish, Tom Petty T-shirts emblazoned with eab logos, show books thick with Dean Witter ads. There's plenty of tiered seating. The VIP tent, closest to the stage, costs $300 per person. A seat in the VVIP tent costs $600 and up. It includes a fully stocked bar and lavish table settings. Lawn seats, 100 yards from the stage, cost $40.
When Sillerman finally gets to a backstage tent where Petty sits at a littered table with his band, he greets the rocker like an old friend. "So we got a house for you to stay in," says Sillerman, throwing an arm around Petty's shoulder. After some coaxing from his girlfriend, Petty accepts. Sillerman claps his back and says he'll be sitting down front during the show. "So," says Petty with a crooked smile, "we'll be seeing a lot of you tonight." Sillerman tells the grizzled rocker that "people who paid a lot of money are in the front seats." Petty, road-weary and bored, in skinny yellow shades, just nods. He hates tiered seating. And he'll gladly fight about it. But not at a benefit show. Sensing Petty's lack of enthusiasm, Sillerman assures him that after a few songs, "we open the VIP section" and the crowd moves up front. "Great," says Petty, "so we won't just be playing to the rich all night."
When Petty takes the stage in a long velvet coat and white ruffled shirt, he surveys the VIP area, choked with lawn chairs and coolers tripping up dozens of cheap-seat fans who are already breaking ranks. "Everybody that sees a folding chair," says Petty, "let's stomp it to death." The crowd cheers -- and stomps -- as Petty launches into "I Won't Back Down." Sillerman, front-row center, remains seated as the dancers surge and bump around him, nodding in time to the music with a satisfied grin.