An appealingly scruffy-looking young actor with curly dark hair and piercing green eyes who co-starred with perky young teen queen Melissa Joan Hart in the high school-set romantic comedy "Drive Me Crazy" (1999), Adrian Grenier seemed poised to claim the teen idol crown. Prior roles in such highly-regarded independents as "Hurricane Streets" (1997) and "The Adventures of Sebastian Cole" (1999) would point to a more enduring and challenging career in store for the young actor. Grenier made his feature debut in Hannah Weyer's 1997 independent "Arresting Gena" and that same year played a street punk in "Hurricane Streets". 1998 saw him take a role as part of superstar Brandon Darrow (Leonardo DiCaprio)'s entourage in Woody Allen's "Celebrity". Grenier's next outing was "The Adventures of Sebastian Cole", starring as the title character. His portrayal of the confused but good humored young man struggling through his stepfather Hank's decision to become Henrietta as well as his own pubescent trials in 1983 upstate New York. The actor impressed critics and audiences with his charming turn, and proved more than capable of holding his own onscreen.
Grenier's next project was in quite a different vein from his previous work, starring as an edgy activist turned dream date to girl-next-door Nicole (Melissa Joan Hart) in "Drive Me Crazy". He performed well in the film and affected the perfect detached too-cool-to-care facade that teenage girls expect in a heartthrob. For his next role in John Waters' "Cecil B Demented", he portrayed an actor, the leading man in the titular director's latest schlocky offering "Raving Beauty". Grenier returned to hallowed halls, this time as a college student gone wrong in James Toback's "Harvard Man" (2001). Cast opposite Sarah Michelle Gellar, another teen favorite, he played the eponymous basketball star who falls into a life of compulsive gambling and drug abuse.
The actor then took on a series of supporting roles in high-profile projects featuring A-list talent, including Steven Spielberg's "A.I." (2001), opposite Bruce Willis and Colin Farrell in "Hart's War" (2002), and Woody Allen's "Anything Else" (2003), while still snaring leading roles in smaller projects, such as the romantic mystery "Bringing Rain" (2003). But it would be his leading role as movie actor Vincent Chase on the HBO series "Entourage" (2004 - )--loosely based on the antics and exploits of series creator Mark Wahlberg's hangers-on--that would provide Grenier with his most visible vehicle. He was next set to play Anne Hathaway's love interest in the fashion industry tell-all film "The Devil Wears Prada" (lensed 2005) which also starred Meryl Streep.
In addition to his acting career, at the 2002 Tribeca Film Festival, Grenier debuted his documentary "Shot in the Dark" (2002), which chronicles his search for his biological John Dunbar, who was never married and from whom he remains estranged.