Jerry attended the Professional Children's School in his native Manhattan, where his classmates included actors Tara Reid, Sarah Michelle Gellar, and Macaulay Culkin. He went on to major in film at New York University in 1992, graduating in 1995 with a Bachelor of Fine Arts.
During a summer vacation from NYU, Jerry starred in Calendar Girl (1993), alongside Jason Priestley. O’Connell gained higher exposure in the blockbuster films Jerry Maguire in 1996, co-starring Tom Cruise and a then-unknown Renée Zellweger; and Scream 2 in 1997, with Courteney Cox and Neve Campbell. He also had a cameo role in the 1998 teen flick Can’t Hardly Wait, starring Jennifer Love Hewitt. For a starring role as Joe in the 1996 film Joe’s Apartment, Jerry adventurously opted to let live cockroaches crawl inside his mouth instead of synthetic ones. In 2003, Jerry starred in Kangaroo Jack, a film about a mob-deal gone wrong when a kangaroo ends up on the run with the funds. The film also starred Christopher Walken, whom Jerry learned to impersonate on-set. In 1999, Jerry sold his first screenplay, First Daughter, which became a film in 2004 starring Katie Holmes as the daughter of the president of the United States.
Throughout his college years, Jerry appeared in various television series, including Camp Wilder in1992, with Hilary Swank and the futuristic sci-fi series Sliders from 1995 to 1999, for which he passed up a role on hit-TV series Party of Five. Jerry served as producer during his fourth and final season with Sliders, writing and directing several episodes. Jerry currently stars on NBC’s Crossing Jordan as Detective Woody Hoyt.
Jerry’s career has also included a few departures from film and television series. In 1999, he starred as Mariah Carey’s two-timing boyfriend in a 1999 video for her song "Heartbreaker." He was also featured on a 2005 home makeover episode of the Oprah Winfrey Show, in which his bachelor pad is gutted and made-over by interior designer Nate Berkus.
Jerry’s older brother, Charlie O’Connell, who is also an actor and bears a striking resemblance to Jerry, was featured on reality-TV show The Bachelor in 2005 and has also appeared in Sliders. The brothers shared a condo for several years in New York before having a falling out in 2000. Jerry announced, "We decided to cut the cord between us," and moved into the condo upstairs.
Jerry has been romantically linked to former Spice Girl, Geri Halliwell, as well as fellow actress and former classmate, Sarah Michelle Gellar. He got engaged to Rebecca Romijn in September 2005, six months after the actress was officially divorced from actor John Stamos. When asked about his engagement, Jerry commented, "I still can't believe she said yes when I asked her to marry me. I keep waiting for Ashton Kutcher to tell me I'm being Punk'd."
YUDDY
