Jubilantly single Jerry O'Connell creates major ripples on TV, in movies and with women

How does Jerry O'Connell charm so many women? Let us count a few of the ways. Method 1: The Corny Opening Line, as in O'Connell's greeting to Crossing Jordan star Jill Hennessy his first day on the NBC show's set last season as Boston police detective Woody Hoyt. "He looked me up and down," she recalls, "and said, 'Wow, Jill Hennessy, I didn't know you were such a tall drink of water!' " Method 2: The Schoolboy Prank, as played last year on Estella Warren, O'Connell's costar in the new Australian caper comedy Kangaroo Jack. "There are a lot of snakes in the Outback," Warren says, "so Jerry would constantly come up behind me going 'Sssssss' and grab my leg or ankle."

"Things could not be easier for me," says O'Connell (outside his L.A. condo). "I could not be more overpaid for doing something that is fun."

Surprisingly, both approaches seem to have worked. Though Hennessy is happily married, than you, she lapped up O'Connell's attentions. "I just said, 'Keep talking, Jerry, keep talking!' This guy makes me feel so good." And he even managed to snake-charm Warren, who briefly dated him after shooting wrapped. "We have stayed close friends," she says.

He also remains "very good friends" with Olympic swimmer Janet Evans, whom he dated last summer, and previously went out with Sarah Michelle Gellar. Still, for being a prolific ladies' man, O'Connell, 28, says, "I'm not mentally ready for any serious relationship. I'm not very good at them."

"He just has to meet the right person," says Kangaroo Jack's Estella Warren.

Besides, says the 6'2" actor, whose career has spanned film (Jerry Maguire, Scream 2) and TV (Sliders), "it's a common complaint with girls I date that I spend too much time with my brother." His brother Charlie, 27, a model and actor who costarred in Sliders, had been sharing a Hollywood Hills condo with him. But in July 2000, "we decided to cut the cord between us," says Jerry. So he moved into the condo upstairs. The two units even share the same key. Whenever their parents, Michael, 70, an advertising art director, and Linda, a Jersey City, school teacher, 60, both retired, come out to visit from Manhattan, they take Jerry's apartment and he crashes at Charlie's.

Back when they were growing up in New York City, Linda O'Connell kept both her sons busy with everything from ballet to drama to fencing. O'Connell says he was a "hyperactive" sixth grader when director Rob Reiner was casting for, in Reiner's words, "a chubby little kid who was kind of goofy" to costar in 1986's Stand by Me. Meeting Reiner, then best known as an actor on All in the Family, "I was shocked," says O'Connell. "I was like, 'You're 'Meathead!' " Then, recalls Reiner, "he walks out. And I thought, 'This is one of the funniest, wackiest kids I've ever met.' "

"We know how to push each other's funny buttons," says O'Connell of sib Charlie.

"That same manic behavior that I'd been getting in trouble for was totally rewarded on the set," says O'Connell. "I felt like I had found my niche." Soon after graduating from New York University's film school in 1995, he moved to LA and began working steadily. But Crossing Jordan's Det. Hoyt "is really fun," he says, "because it's the first adult role I've ever played where I put on a suit every day." The part may be rubbing off in real life. "He doesn't party as much," notes brother Charlie, "and he works out on a daily basis. It's a step towards adulthood. If he wants to mess things up, he comes down to my place."


He visits often. "Relaxing," says Jerry, "is being with my brother." And what'll happen if one or both, egads, get married? Simple, says Jerry. "I'll go to his wedding, be really supportive, and then he and his wife and me and my wife will probably get a big duplex." In the meantime, says Charlie, "I keep his seat open on the couch if he ever wants to come back."

- Michael A. Lipton
- Elizabeth Leonard in Los Angeles