- 2008: Played the titular role in the film version of the video game "Max Payne"
- 2008: Nominated for the 2008 People’s Choice Award for Favorite Leading Man
- 2008: Co-starred in M. Night Shyamalan's "The Happening"
- 2007: Co-starred with Joaquin Phoenix and Robert Duvall in "We Own the Night"
- 2006: Cast in Martin Scorsese's mob drama, "The Departed" a remake of the popular Hong Kong crime thriller "Infernal Affairs"; received Golden Globe and Oscar nominations for Best Supporting Actor
- 2005: Starred in John Singleton's "Four Brothers" as one of four brothers out to avenge his mother's murder
- 2004: Starred opposite Jude Law and Naomi Watts in "I Heart Huckabee's"; re-teamed with director, David O. Russell
- 2004: Executive produced the HBO series "Entourage" which centers on film star Vince Chase (Adrian Grenier) and his close circle of friends; earned Emmy (2004, 2005) nominations for Best Comedy series
- 2003: Co-starred with Charlize Theron in F. Gary Gray's remake of the heist film "The Italian Job"
- 2002: Co-starred in Jonathan Demme's remake of "Charade" titled "The Truth About Charlie"
- 2001: Starred in Tim Burton's remake of "Planet of the Apes"
- 2001: Played a salesman who becomes a heavy metal singer in "Rock Star"; Clooney was one of the film's producers
- 2000: Reunited with Clooney as co-stars of Wolfgang Petersen's gripping fact-based sea thriller "The Perfect Storm"
- 2000: Starred in the New York City-set crime drama feature "The Yards"
- 1999: Teamed with George Clooney and Ice Cube in David O Russell's acclaimed Gulf War chronicle "Three Kings"
- 1999: Played an idealistic NYPD recruit opposite Chow Yun Fat's veteran cop in the crime thriller "The Corruptor"
- 1997: Earned positive reviews as 1970s porno star, Dirk Diggler in Paul Thomas Anderson's "Boogie Nights"
- 1997: Had a starring role of an Irish con man in the little-seen independent "Traveller"
- 1996: Starred in the teen thriller "Fear" as the violently obsessive boyfriend of Reese Witherspoon
- 1995: Breakthrough role as the hot-tempered best friend of Leonardo DiCaprio's Jim Carroll in "The Basketball Diaries"
- 1994: Made film debut with a featured acting role in "Renaissance Man"
- 1993: Made guest appearance on "The Ben Stiller Show" (Fox)
- 1993: TV-movie acting debut, "The Substitute" (USA Network)
- 1992: Signed a two-year contract as Calvin Klein underwear model
- 1991: Debut album, Music for the People; recorded with his band The Funky Bunch; album went platinum
- 1988: Arrested for assault and jailed for 45 days
- 1986: Unwilling to take singing lessons, he quits New Kids on the Block after six months
- 1985: He and brother Donnie became first two members of the teen vocal group, New Kids on the Block
- 1984: Started breakdancing on Boston streets




