Kennedy is best known for his breakthrough performance as Randy Meeks, the video store clerk well-versed in the conventions of the scary movies, in Wes Craven's 1996 self-referential horror film "Scream" and its follow-up "Scream 2" (1997).

Jamie Kennedy was cast in the little-seen 1995 indie comedy "The Road to Flin Flon". An appearance as a punked-out rival to John Leguizamo in "William Shakespeare's Romeo and Juliet" (1996) and as a street hustler who attacks Greg Kinnear in the Oscar-nominated "As Good As It Gets" (1997) can be counted among his smaller roles.

This offbeat, high-energy actor frequently sports a shock of peroxide blond in his short brown hair and has cultivated a rumpled hipster look complete with colorful eye-catching shoes reportedly culled from the set of "Scream". His laid-back yet edgy persona and dynamic performances have earned him an impressive fan following. Following his success in "Scream", Kennedy took on roles in the 1997 films "Sparkler", as one of a trio of youths headed to Las Vegas, and "Clockwatchers", as the office mailman who develops a crush on a temp worker. He continued to add to his gallery of eccentric characters with a dramatic turn as a heroin addict in "Bongwater" and a novice screenwriter in the comedy "Starf*cker" (both 1998). He added much-needed comedy in the dramas "The Three Kings" (1999) and "The Boiler Room" (2000). After years of obtaining his fair-share of supporting and featured roles, Kennedy was given his own sketched comedy show.

In 2002, The Jamie Kennedy Experiment  a television show that can best be described as a combination of Candid Camera and Saturday Night Live, was born and quickly became The WB's highest ranking new show.

In 2003, "Malibu's Most Wanted" was released starring Kennedy as the white "wanna-be rapper" from Malibu. Kennedy was set to elevate his profile with "Son of the Mask" (2005), the sequel to the blockbuster Jim Carrey vehicle. In the movie, Kennedy played a cartoonist who finds the Mask of Loki and later has a son that possesses some of its spectacular powers. Loki, however, comes down to earth and engages Kennedy in an epic power struggle.