O'Connell starred as Detective Woody Hoyt on the NBC crime drama Crossing Jordan (2001) until its cancelation in May 2007, and was engaged to actress Rebecca Romijn. O'Connell served as executive producer and received a "story by" credit on the film, which starred Katie Holmes and Michael Keaton. The film was released in 2004 by 20th Century Fox-based Davis Entertainment. O'Connell has also tried his hand at screenwriting and sold his first screenplay, for First Daughter, to New Regency in 1999. O'Connell has since gone on to star in such movies as Jerry Maguire, Body Shots, Mission to Mars, Tomcats, Scream 2, and Kangaroo Jack. He served as producer during his fourth season, and is credited with writing and directing several episodes. He was offered the role of Quinn Mallory in the series, which ran for three seasons on Fox and two seasons on the Syfy Channel. During his junior year, O'Connell auditioned for the television pilot Sliders (also filmed in Canada). He also appeared in the short-lived ABC sitcom Camp Wilder, with Jay Mohr, and Hilary Swank in 1992. During a summer break from NYU, Jerry starred in the feature film Calendar Girl alongside Jason Priestley and Gabriel Olds. He starred in the Canadian science-fiction sitcom My Secret Identity from 1988 to 1991 as the teen hero who develops superhuman traits. In 1987, O'Connell appeared in a commercial for Frosted Flakes.
Shortly after turning eleven, he landed his first feature film role as the character Vern Tessio in Rob Reiner's Stand by Me. As a child, he did commercial work for Duncan Hines cookies. O'Connell began his acting career at a young age. While there, he studied screen writing and competed on the fencing team, serving a stint as captain of the sabre squad. He attended New York University from 1991 to 1995, majoring in film.
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As a teenager, he attended Manhattan's Professional Children's School. O'Connell was raised in Manhattan with his younger brother, actor Charlie O'Connell. He is half Irish, one quarter Italian, and one quarter Polish ancestry. O'Connell was born in Manhattan, the eldest son of Linda, an art teacher, and Michael O'Connell, an advertising agency art director originally from the United Kingdom.