For sheer jaw-dropping home-court advantage, few tennis courts can rival the newly built surface at the Benedict Canyon home of investor James Goldstein. Known for his John Lautner-designed house (which cameos in The Big Lebowski) and for sitting front row at European fashion shows in head-to-toe Cavalli, Goldstein recently completed construction on what can only be described as an infinity tennis court. Situated atop a new two-story structure that will include a home nightclub, the court -- bounded on the south by nothing but an unframed 42-inch-high glass partition -- appears to rush out to meet the Westside horizon. "I thought there would be more of a problem with losing balls, but it really hasn't been an issue," says Goldstein.
In Hollywood, though, it's not just about the court but who's holding court. Ever since 10-time Grand Slam champion Bill Tilden came to town in the 1920s to volley with friend Charlie Chaplin, power serves have gone hand in hand with power schmoozing. Whereas the biz's other key social sport, golf, revolves around country clubs such as Riviera and Bel-Air, the creme de la creme of tennis games take place in a more exclusive setting: people's private domains. From Malibu Colony -- where Lighthouse Entertainment's Steven Siebert and his wife, Gersh partner Leslie, run an annual tournament -- to Friends With Benefits producer Martin Shafer's Brentwood spread, dinner invites are easy compared to gaining entree to this scene. And sharing a meal doesn't compare to the bonding -- important in a relationship-based industry -- that the friendly but intense competition can spark.
"I play 99 percent of the time at my court. You get a little lazy when people are willing to come to your house," says Shafer. Those people include regular compatriots Sony CEO Michael Lynton ("He can run down anything"), screenwriter Stephen Gaghan and Warner Bros. general counsel John Rogovin. UTA agent David Melmed, a former college player, also sees net time there.
For Shafer, Hollywood and tennis long have intertwined. As a teen, he got invited to play at Charlton Heston's house above Coldwater Canyon. "He loved tennis," says Shafer. "The great players, when they were in town -- Rod Laver, Ken Rosewall -- would come and play." Later, Shafer got to know Andrew Scheinman and Rob Reiner, with whom he'd eventually co-found Castle Rock, during matches at Norman Lear's house.
The most legendary insiders' club is the one at Woodland, Bob Evans' Beverly Hills estate. In three decades, the producer has hosted matches involving everyone from Barbra Streisand and Kirk Kerkorian to Ted Kennedy and John McEnroe. "If I had a percentage of deals made on this court, I'd be living in San Simeon," says Evans.
Among the industry names who currently hit ground strokes at his spread are DreamWorks co-president of production Mark Sourian, Benderspink's J.C. Spink and New Line president Toby Emmerich. The matches are organized by Darryl Goldman, a pro who has held the unique-for-a-private-residence post of tennis director for 27 years. Goldman recalls the time Brett Ratner popped by with then-girlfriend Serena Williams for a surprise morning visit. As Goldman -- who was hitting with a group of entertainment lawyers including Disney general counsel Alan Braverman -- tells it: "Serena was in her bathrobe sitting and watching these guys play. They never worked harder in their life." (Installing a tennis court can cost at least $50,000 -- if not $100,000 -- and top pros these days charge $100 to $150 an hour.)
The Hamptons have their own tennis tribes. Alec Baldwin is a regular at Lorne Michaels' house, and a group of 10 women -- including publicist Peggy Siegal, Tory Burch, Cristina Cuomo and SiriusXM host Perri Peltz -- shuttle among one another's home courts during the summer. "In the winter, we eat lunch at the Four Seasons. Our idol Billie Jean King comes, and she gives us life advice," says Siegal. "We support each other in each other's work, but on the court we're highly competitive."
Lawyer Skip Brittenham and manager Chuck Binder also host games at their houses in Los Angeles. Compared to golf, says Binder, "It doesn't take up the whole day -- that's what I like about it." Adds ICM agent and former junior player Chuck James, a frequent guest on the Malibu Colony scene: "Most of the people I know are in a tennis situation in their day-to-day. You have to be mentally acute. It's a sort of matchup with their jobs."
Having a clay court, which is uncommon, can be a draw. Knots Landing star Donna Mills, who has one at her house in Brentwood, has no problem attracting enthusiasts to the round-robin tennis parties she throws year-round.
The Sieberts take over six courts in Malibu Colony for their July 4 tournament. "There are usually 100 people, and our house is the clubhouse. We give trophies, and it's so competitive that people bring in ringers," says Leslie Siebert.
Sourian, who has become an avid player the past few years, sees no need to join a club, not when he has the honor of playing at Evans' court. "It's sort of like the L.A. dream. It's as close as you can get to tradition in Hollywood," says the exec. And though he says he hasn't made any deals based on relationships developed there, he admits, "If I did, it certainly would be easier because there's a familiarity and a warmth that you wouldn't otherwise have."
Sourian also recalls meeting Evans soon after he was invited to the court through Spink, a friend: "There's never an official vetting, but at some point you do meet the big guy. It's never said, but you get the feeling you might not get a time slot if it doesn't go well."