Kennedy first broke through in 1996 with Scream, playing horror-obsessed teen Randy Meeks, the film’s comic relief. Though he was relatively unknown at the time, director Wes Craven championed him for the role over more established names like Jason Lee and Seth Green.
As his career gained momentum, Kennedy shared the screen with A-listers including Leonardo DiCaprio, George Clooney and Mark Wahlberg. In 2003, he headlined and co-wrote the cult comedy Malibu’s Most Wanted alongside writers including Nick Swardson.

During his recent outing, Kennedy’s once-boyish look was largely concealed by a thick salt-and-pepper beard. Dressed casually in sweatpants and an Adidas jacket, he completed the look with a baseball cap, necklace, and his longer hair tied back in a ponytail. At one point, the Pennsylvania native was seen hopping onto a Lime scooter.
Kennedy’s early Hollywood hustle has become the stuff of legend. Struggling to land roles in the ’90s, he famously invented a fake agent named “Marty Power,” pretending to represent himself over the phone to secure auditions. Eventually, his persistence paid off when Craven cast him in Scream, recalling how he had once taken a chance on an unknown Johnny Depp for A Nightmare on Elm Street.
Kennedy reprised his role as Randy in the sequel before the character met his end at the hands of Ghostface. Around the same time, he appeared in Romeo + Juliet, directed by Baz Luhrmann, and in the Gulf War drama Three Kings.

One of his most enduring fan favorites remains Malibu’s Most Wanted, in which he played B-Rad, a wealthy politician’s son desperate to become a rapper in the style of Eminem. The film, which also featured Snoop Dogg, Taye Diggs, Anthony Anderson, Regina Hall and Ryan O’Neal, was a box office success despite mixed reviews.
He also fronted the prank series The Jamie Kennedy Experiment in the early 2000s. Not all projects were hits, however — his leading role in Son of the Mask earned Razzie attention.

More recently, Kennedy appeared in the 2021 drama Roe v. Wade, which sparked speculation about his political views due to its conservative-leaning cast. He later clarified that he supports abortion rights and took the part as a rare dramatic opportunity, noting that sharing a project with certain actors does not define his personal beliefs.
In 2022, he made a voice cameo in the Scream reboot and continues to work steadily, with upcoming projects including the comedy Lunch Hour, starring Alan Cumming and Thomas Middleditch.