Long Island, New York native Kevin Connolly broke into feature films and blockbuster television series roles by way of commercials; the fresh-faced star later recalled that he hawked every brand from Chips Ahoy! to Parker Brothers in front of the cameras during his early years. Cresting on this exposure, Connolly moved into bit roles in features during adolescence and gradually ascended to supporting billing. Projects in which he appeared included Rocky V (1990), The Beverly Hillbillies (1993), Angus (1995), and John Q. (2002). Connolly received elevated attention courtesy of his well-received supporting turns as Slim in the Denzel Washington-directed psychological drama Antwone Fisher (2002) and Fin in the nostalgic romance The Notebook (2004), but achieved widespread acclaim with his portrayal of Eric Murphy, one of several young men enjoying the perks of Hollywood stardom, in the HBO comedy series Entourage from 2004 to 2011. After the show ended its run, Connolly reentered the world of film, appearing in a number of projects, like the Ken Kwapis-directed romantic comedy He's Just Not That Into You, and the horse-racing drama Secretariat.
Connolly made his feature directorial debut in 2997 with the black comedy The Gardener of Eden, executive produced by Leonardo DiCaprio.