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In the Jennifer Jason Leigh and Alan Cumming directed comedy The Anniversary Party (2001), he played director Mac Forsyth. The box office hit The Perfect Storm was his only release of 2000 and featured Reilly as a veteran crew member on the Andrea Gail fishing vessel which was caught in the 1991 Perfect Storm. In Sam Raimi's sports drama For Love of the Game, released the same year, Reilly played fictional baseball catcher Gus Sinski. That same year, Reilly played one of the newspaper managing editors in the romantic comedy film Never Been Kissed. In 1999, Reilly starred in the independent film The Settlement alongside William Fichtner, which Variety writer Robert Koehler dismissed as a "write-off" despite praising his performance. Terrence Malick's ensemble war film, The Thin Red Line (1998) featured Reilly in a supporting role that was written as a larger one, but much of his scenes were deleted along with many other cast members. Reilly collaborated with Anderson on other films, playing a pornographic actor in Boogie Nights (1997) a deeply religious police officer in Magnolia (1999) and a cameo in the music video for Fiona Apple's single "Across the Universe". In Paul Thomas Anderson's directorial debut film Hard Eight (1996), Reilly played a near homeless man in Reno, Nevada, who is taken under the wing of a senior gambler ( Philip Baker Hall). In 1995, Reilly appeared in the psychological thriller Dolores Claiborne as a police constable and in the drama Georgia as a drug-addicted drummer in the band Jennifer Jason Leigh's character joins. His next role was in The River Wild (1994), in which Reilly appeared alongside Kevin Bacon as a pair of criminals who terrorise a family during a rafting trip. Reilly appeared in a supporting role in What's Eating Gilbert Grape (1993), playing one of the titular character's (played by Johnny Depp) friends. In 1992's Hoffa, Reilly played Jimmy Hoffa's ( Jack Nicholson) associate who testifies against him at Hoffa's trial. That September, he played an Irish hoodlum named Stevie McGuire in the crime film State of Grace, which starred Sean Penn Reilly had previously appeared as a monk in the comedy We're No Angels (1989), which also starred Penn. He played Buck, Tom Cruise's character's NASCAR crew member in Tony Scott's Days of Thunder in June 1990. Although his role was written as a small one, De Palma liked Reilly's performance so much that the role was significantly expanded. Reilly made his film debut in the Brian De Palma war film Casualties of War as PFC Herbert Hatcher in 1989.
Reilly filmography and List of awards and nominations received by John C. Reilly performs with his band John Reilly and Friends and worked as a stage actor in True West (2000), for which he was nominated for the Tony Award for Best Actor in a Play.
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In 2022, he led an ensemble cast for the HBO sports drama series Winning Time: The Rise of the Lakers Dynasty. In 2020, he created and starred in a Showtime comedy series Moonbase 8. The role earned him a Golden Globe Award nomination as well as a Critics' Choice Award nomination. In 2018 he starred as the comedian Oliver Hardy in the biopic Stan and Ollie. Reilly continued to act in independent films such as Cyrus, We Need to Talk About Kevin, and Carnage (all in 2011), as well as Yorgos Lanthimos's The Lobster (2015), and The Sisters Brothers (2018). He voiced the title character in the commercially successful Wreck It Ralph film series (2012–2018), and appeared in the superhero film Guardians of the Galaxy (2014), as well as Kong: Skull Island (2017). Reilly starred with Will Ferrell in the Adam McKay-directed comedies Talladega Nights: The Ballad of Ricky Bobby (2006) and Step Brothers (2008). In 2007, he starred in the comedy Walk Hard: The Dewey Cox Story, garnering him a Grammy Award nomination and a second Golden Globe Award nomination for the song performed in the film, "Walk Hard". He worked with director Martin Scorsese on both Gangs of New York (2002) and The Aviator (2004).
For his performance in Chicago (2002), Reilly was nominated for the Academy Award for Best Supporting Actor and the corresponding Golden Globe Award. He also starred in Paul Thomas Anderson's films Hard Eight (1996), Boogie Nights (1997) and Magnolia (1999), as well as Terrence Malick's The Thin Red Line (1998). After his film debut in Casualties of War (1989), he gained exposure through his supporting roles in Days of Thunder (1990), What's Eating Gilbert Grape (1993) and The River Wild (1994). John Christopher Reilly (born May 24, 1965) is an American actor, comedian, screenwriter, musician, and producer.