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Hollywood's Best Boyfriends

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Jada Pinkett & WILL SMITH

Love Story: The 29-year-old divorced father of a 4-year-old son met 26-year-old Pinkett in 1990 when she auditioned for his NBC show, The Fresh Prince of Bel Air.

Faithfully Hers: “He’s not a player,” says Smith’s Independence Day and Pinkett’s Set It Off costar Vivica A. Fox. “What I love about Will more than anything is that he’s a one-woman man. He loves being in love and in a relationship.”

Fresh Chef: Smith knows the way to Pinkett’s heart is through their L.A. kitchen, where he prepares apple and banana pancakes, fried chicken and sweet potato pies.

Man in Back: A regular but low-key presence on the set when she was filming Set It Off, Smith showered gifts on his sweetheart. “On the first day of shooting, he sent her a massive flower arrangement,” says costar Kimberly Elise. And after Pinkett broke her ankle while walking her four Rottweilers, “he was literally carrying her,” recalls Fox. “He had a lot of things going on, but he was there.”

Barbra Streisand & JAMES BROLIN

Love Story: At 57, he’s a twice-divorced father of two. She’s 55 and the divorced mother of actor Jason Gould. They met in 1996 at a party, where he announced, “I’m taking you home with me.”

Mr. Right: Streisand told USA Today that Brolin is her “dream man. He’s very strong and masculine, yet totally unafraid of his feminine side, totally accessible emotionally.”

Handyman: The son of a builder, Brolin plays Mr. Fix-It in Steisand’s Holmby Hills, Calif., home. “Jim can get out the toolbox and will,” says his manager, Jeff Wald. “He’s the least pretentious guy you’ve ever met.”

Roughing It: Brolin takes his fiancée on road trips where they stay in motels. Back at home, “he’s bought camping equipment, and they’re going to camp in her backyard,” says Wald. “It’s a nice romantic thing to do.”


Love Story: The 31-year-old Single Guy met the 26-year-old country singer at a 1994 celebrity softball game.

Team Players: “I fell in love with her when I saw her hit a ball to right field,” says Silverman, who now plays shortstop to Fery’s second base for the Hollywood Allstars. “We turn a lot of double plays together,” she says.

Mr. Clean: “He’s very tidy,” says Fery. Silverman picks up his clothes and helps with the chores in their Hollywood Hills home.

Ranch Dressing: “He got all this stuff so he would look like a real cowboy when he came to my concerts. It’s kind of funny to see him out there in his little cowboy hat and boots.”

He Can Really Take a Hint: Out browsing with a friend, Fery took a shine to an antique jewelry box. The friend informed Silverman, who persuaded the shopkeeper to open the store after hours so he could buy it for her. “When I got home, it was sitting there,” Fery says. “I thought that was sweet.”

Susan Sarandon & TIM BOBBINS

Love Story: Robbins, 39, and Sarandon, 51, met while filming 1988’s Bull Durham. Though unmarried, they share a deep commitment to political causes and the Manhattan home where they’re raising their two sons, 8 and 5, and her 12-year-old daughter by filmmaker Franco Amurri.

Dead and Alive: “I love him even more than I did when we started,” Sarandon told ENTERTAINMENT WEEKLY after working with Robbins on Dead Man Walking. His direction made her an Academy Award winner. “The best present he could give was an Oscar,” says columnist Cindy Adams.

Man of Her Dreams: “When Susan wants to sleep in, he makes sure he’s up early with the kids and cooks breakfast,” says Sarandon’s brother Terry Tomalin.

Kimberly Williams & PETE SAMPRAS

Love Story: The world’s No. 1-ranked tennis player and the Father of the Bride and Relativity star, both 26, met in April through a matchmaking friend.

Opening Knight: Known for his single-minded pursuit of tennis (“He’d rather have his heart broken than his serve,” says tennis commentator Bud Collins), Sampras broke form during the U.S. Open when he attended her Broadway debut in The Last Night of Ballyhoo. “He tried very hard to avoid grabbing the spotlight,” says her dad, Gurney.

Tarzan Touch: After winning his fourth Wimbledon title in July, Sampras tapped three times on his chest in a coded message to Williams. “It meant, ‘I love you,’ ” the London Observer reported.

Jennifer Love Hewitt & WILL FRIEDLE

Love Story: The 21-year-old star of Boy Meets World and his Party of Five girlfriend, 18, were introduced in 1996 by a friend.

Where There’s a Will There’s TLC: Friedle specializes in foot massages and home cooking. “Will takes good care of himself,” she says, “but at the same time he takes care of me.”

Special Delivery: Hewitt spied an Easy Bake oven in a toy store and took out her wallet. “He talked me out of it,” she recalls. “I was mad at him for an hour!” But the foxy Friedle just wanted to surprise her and later presented the toy with a card saying, “You don’t have to grow up.” Lucky Hewitt describes the gift as just one of “the little things he does to make me feel special.”

Oprah Winfrey & STEDMAN GRAHAM

Love Story: The wealthiest woman in the entertainment industry (worth $415 million, says Forbes), 43, and the 46-year-old head of his own marketing firm met in 1986 at a friend’s party and live in Chicago.

Next Oprah: Women Who Laugh at Their Boyfriends’ Jokes: “Steddie,” as she calls him, has a corny-but-cute sense of humor, which “O” (his pet name for her) revealed on a recent show: “Every time we have artichokes for dinner, he goes, ‘You might choke Artie, but you won’t choke Stedman.’ Every single time!”

He Only Has Eyes for Her: Businessman Graham is a world traveler, but he doesn’t rove. “I’ll even watch him sometimes,” says talk show host Gayle King, Winfrey’s best friend. “Somebody cute will walk by, and I’ll go, ‘I know he’s gonna look!’ And he never does! I think his thing is, ‘When you have the best, why do you want to try other people?’ ”

Terms of Endearment: Graham recently stocked a vacation rental house in New Jersey with her favorite healthy foods, and “he leaves Oprah little notes on her pillow if he or she is going out of town,” says King. “Just things that clearly let her know he’s thinking about her.”

Jennifer Aniston & TATE DONOVAN

Love Story: The voice of Disney’s Hercules, 34, and the Friends star, 28, met through pals in 1995.

Across a Crowded Room: “When we met, it was like this instant click. That had never happened to me before,” Aniston has said of Donovan, who gave her an Australian shepherd mix puppy for Valentine’s Day.

Mr. Congeniality: “If you have a problem, he always knows what to say to put things into perspective,” says Donovan’s mother/Eileen. “He’s a very level person.” Agrees his friend, musician Jay Gibson: “He’s a very supportive friend, so it doesn’t surprise me that he’s also a very supportive boyfriend.”

Jealous Lover: Aniston guest-starred on his 1995 show Partners—as costar Jon Cryer’s love interest. “It was torture. All she did was make out with the guy,” recalls Donovan. “It was totally weird.”

Not Another Silly Love Song: “All Jennifer wants is for me to write her a song,” Donovan, who plays fiddle in a small Irish band, has said, “and I cannot come up with one.”