Trivia

Author of the book 'Wannabe: A Hollywood Experiment' detailing his miserable early showbiz career before masquerading as his own agent brought him success.

Was in a relationship with Jennifer Love Hewitt [March 2009 to March 2010].

The youngest of 6 children - 1 brother, 4 sisters

Was considered for the role of Bob Sugar in Jerry Maguire (1996).

Kennedy was criticized for his decision to appear in the conservative film Roe v. Wade (2019). He said many of the far-right personalities who appear in the film shot their scenes late in production and he was not aware they would be appearing in the same film. In an interview with 'The Daily Beast', Kennedy said he took the role as an acting challenge and he is personally pro-choice and that, "it's also not fair for people to think that because I'm in a project with them that I'm like that, or that I believe in this stuff. That's not fair." (To which the interviewer responded, "If someone popped up in Triumph of the Will (1935), I would probably assume that they don't like Jews very much.").

Though he has same last name he is not a member of the famous Kennedy family he is also not in any way related to the late Oscar winning actor George Kennedy.