A native of Chicago, where he was born May 24, 1965, Reilly broke into film in 1989, the year he starred in Casualties of War and We're No Angels, both of wh... ich featured Sean Penn and a less than stellar reception. Reilly subsequently spent the early '90s appearing in films of every conceivable genre, from the Tom Cruise testosterone extravaganza Days of Thunder (1990) to Woody Allen's Shadows and Fog (1992) to What's Eating Gilbert Grape (1993). Thanks to his unglamorous appearance, Reilly also did an obligatory turn as a backwoods psycho, popping up alongside Kevin Bacon in The River Wild (1994) long enough to freak out Meryl Streep and her family. 1996 marked the beginning of Reilly's collaboration with director Anderson.

That year, he starred as a none-too-bright loser stranded in Vegas in Hard Eight, Anderson's feature-length directorial debut. Reilly earned wide praise for his work in the film, which went largely unseen by audiences. The same couldn't be said of Reilly and Anderson's second collaboration, Boogie Nights, the following year. One of the most critically lauded films of 1997, it featured Reilly as another loser, a dim porn actor with dreams of becoming a magician/songwriter.

Thanks to the film's success, Reilly finally earned a bit of long-overdue recognition, as was evidenced by his subsequent casting in Terrence Malick's adaptation of The Thin Red Line (1998). The actor's visibility further increased the following year, thanks to prominent roles in no less than four films. One of these was Magnolia, Anderson's follow-up to Boogie Nights. Like his previous film, Magnolia boasted a large ensemble cast of first-rate actors; among them, Reilly stood out as a lonely police officer who becomes involved with an emotionally unstable woman.

With his career continuing to build momentum, Reilly was next cast alongside George Clooney and Mark Wahlberg in the 2000 big-budget adaptation of the best-selling book The Perfect Storm. However, his biggest year to date came in 2002. Not only could Reilly be seen in prominent roles in four high-profile films, but his scene-stealing turn in the musical Chicago netted him his first Academy Award nomination. Riding high on his escalating stardom, Reilly spent 2003 hard at work on three big releases, The Aviator, Dark Water, and Criminal. Of Reilly's 2004 projects, Criminal arrived first - in September of that year. A remake of the late Argentinian director Fabian Bielinsky's debut crime, the American version tells the story of a couple of scammers ({$Reilly and Diego Luna) who con members of the Beverly Hills upper-crust, the picture (brought to fruition by Steven Soderbergh) received average to positive reviews. On the enthusiastic end, The Los Angeles Times's Carina Chocano called the picture "funny, original and very well observed," and The Philadelphia Inquirer's Carrie Rickey remarked, "Gregory Jacobs' zircon remake of that glowing Argentine gem Nine Queens is the film equivalent of Chinese boxes or Russian matrushka dolls. If you've never played with them before, then there's a prize inside for you.

" Less enthused was The Charlotte Observer's Lawrence Toppmann, who compared the film somewhat unfavorably to its original: "a watered-down version of the same pleasures." Issued in December 2004, Martin Scorsese's The Aviator fared immeasurably better (with critics and at the box) and left in its wake the most enduring legacy of Reilly's 2004 efforts. As Noah Dietrich, the individual who manages Howard Hughes's (Leonardo di Caprio) business affairs, Reilly contributed to a strong ensemble cast that included Cate Blanchett and the splendid Alan Alda. Dark Water, Walter Salles's gothic horror opus, hit cinemas in July 2005.

As the real estate agent who leases young mother Jennifer Connelly a possessed New York City apartment, Reilly delivers effective and substantial menace, even as the motion picture divided critics. In 2006, Reilly starred in two key A-list releases. Released in June 2006, Bob Altman's Garrison Keillor cinematization A Prairie Home Companion lays out a "genial" Altmanesque tapestry of the backstage shenanigans at a fictionalized version of Prairie, that transpire between the cast members. Reilly (who established himself with such force in Altman protege Paul Anderson's similar films) portrays Lefty, one half of a cowboy duo opposite Woody Harrelson's Dusty; they bicker throughout the film and ultimately perform a dirty-lyrics musical number together.

The picture opened, almost unanimously, to glowing reviews. The supporting cast includes Keillor, Meryl Streep, Lindsay Lohan, and Kevin Kline. Reilly showcased his versatility by following up his work in the Altman film by co-starring opposite Will Farrell in the NASCAR comedy Talladega Nights: The Ballad of Ricky Bobby.