If there were such a thing as a "Brat Pack" of the 1990s, the boyishly handsome Josh Charles could have claimed membership. Starting out as a 10-year-old stand-up comic, the Baltimore-born Charles burst out of the Hollywood gate as the lovestruck schoolboy Knox Overstreet, one of Robin Williams' "Dead Poets Society" (1989). He co-starred with Christina Applegate in "Don't Tell Mom the Babysitter's Dead" (1991) and as a closeted college student, he charmingly romanced both Stephen Baldwin and Lara Flynn Boyle in "Threesome" (1994). A certain type of fan adored the quirky Charles as an intelligent and acquired taste, never more so than as Dan Rydell, a co-anchor of Aaron Sorkin's groundbreaking, short-lived "Sports Night" (ABC, 1998-2000). The perennial nice guy proved he could play badass cops in the action hits "S.W.A.T." (2003) and "Four Brothers" (2005), but found his strongest roles on stage as a prolific theater actor, as well as on television in such projects as "In Treatment" (HBO, 2008- ) and "The Good Wife" (CBS, 2009- ), where he essayed an attorney and longtime friend secretly in love with colleague Julianna Margulies. Whether it was his offbeat career choices or non-threatening persona, Charles never quite achieved A-list stardom, but as a consolation prize, built a long-lasting career and earned a lifetime of goodwill from fans of his work through the decades.

Born Sept. 15, 1971 in Baltimore, MD, Joshua Aaron Charles was the son of Laura, a gossip columnist for the Baltimore Sun, and Allan Charles, a commercial director. The couple would divorce0 in 1982. A first baseman in Little League, Charles was always passionate about sports, especially his hometown teams. Notorious in his school for being the class clown, Charles visited a comedy club at age 10 and heckled the onstage entertainment, earning himself a performance slot. After cutting his teeth in stand-up, the youngster chose performing over baseball for his vocation when he attended the famous Catskills theater camp, Stagedoor Manor. Charles enjoyed the experience so much he ended up spending the next four summers there. For high school, he attended the Baltimore School for the Arts alongside fellow future celebrities Jada Pinkett Smith and Tupac Shakur.

Charles began landing film roles while still in high school, debuting briefly in John Waters' love letter to integration and dancing, "Hairspray" (1988) as Iggy, a member of The Corny Collins Show Teen Council. The film, starring Ricki Lake and Divine, was among the mustachioed director's most commercial and best reviewed, and countless audiences Mashed Potato'ed along at home with Charles and the warm-hearted movie. An even bigger success, both critically and commercially, followed when Charles played Knox Overstreet, one of the "Dead Poets Society" (1989) who benefits from the passionate and unorthodox teaching methods used by Robin Williams. A launching pad for Ethan Hawke and Robert Sean Leonard as well as for Charles, the Oscar-winning movie gave the actor a star-making part as a likable, lovestruck boy who discovers his talent for poetry and the rewards of wooing women with his words. The actor continued to land high-profile projects, including the award-winning civil rights drama, "Murder in Mississippi" (NBC, 1990), in which he played one of the three real-life activists famously slain by the Ku Klux Klan in 1964.

Lighter fare followed, when Charles charmed as Bryan, a sweet Clown Dog employee who wins over Christina Applegate in the teen-power comedy "Don't Tell Mom the Babysitter's Dead" (1991). A modest box office success, the film became a cult favorite and a generational touchstone for young fans who delighted in the fantasy of a teen girl getting the high-powered corporate job and the guy, thanks to a little résumé-fudging and a lot of colorful early-1990s fashions. Charles then played to his strengths as a sensitive would-be writer on the cusp of adulthood in Mike Binder's friends-till-the-end charmer, "Crossing the Bridge" (1992), as well as portraying the nephew of a retired baseball pitcher in "Cooperstown" (TBS, 1993), a likable but lower-quality riff on "Field of Dreams."

His most substantial film role since "Dead Poets Society," however, came in 1994, when he was cast as Eddy, an in-the-closet college student who becomes part of a "Threesome." A modern twist on the classic romantic triangle, the film follows a trio of roommates as they become entangled: the bookish Eddy is in love with jock Stuart (Stephen Baldwin), who lusts after the actress Alex (Lara Flynn Boyle), who longs for Eddy. While critical response was lukewarm, the film's target younger audiences adored the film and its gentle depiction of the wonders of college life and love, including honest depictions across the sexual spectrum. Instead of capitalizing on the shock value of its concept, the film focused, with great warmth on the friendship shared by Charles, Boyle and Baldwin, and many fans remembered it as a fond - if flawed - time capsule of the era. "Threesome" was notable as well during its time for featuring a gay main character who was respectfully, non-stereotypically and lovingly depicted, and the appealing Charles earned many kudos for his performance.

Charles's upward career momentum, which had kicked off so impressively, slowed as he began to languish in the lower levels of late-1990s independent cinema. An uncredited role in the buzzed-about indie "Things to Do in Denver When You're Dead" (1995) failed to pay off when the heavily hyped film bombed at the box office, and neither audiences nor critics fell in love with the horror-comedy "The Grave" (1996) or the aspiring traffic reporter comedy "Pie in the Sky" (1996). The success of the dishy "Norma Jean & Marilyn" (HBO, 1996) gave Charles a boost by playing Eddie Jordan, an actor in love with the iconic Marilyn Monroe (Mira Sorvino), but the soapy production was marred by several historical inaccuracies. Leading roles in a string of little-seen, low-budget films followed, memorable only to diehard fans - although the sci-fi/fantasy "Crossworlds" (1997) and the overly talky romantic comedy "Little City" (1997) were enjoyable in a rainy-Saturday-afternoon way. Professional redemption arrived when Charles was cast as one of the stars of Aaron Sorkin's groundbreaking "Sports Night" (ABC, 1998-2000).

A lifelong sports junkie, Charles played the witty, neurotic Dan Rydell, a co-anchor alongside Casey McCall (Peter Krause) of the titular program, which was very much in the vein of ESPN's SportsCenter. Blessed with an amazing cast - besides Charles and Krause, the stars included Felicity Huffman and Robert Guillaume - and Sorkin's top-drawer writing talent, the show was a comedy/drama hybrid that was one of the smartest, most rewarding projects on television at that time. While critics and a small, loyal audience raved about its brilliance, ABC and most viewers did not know what to make of the show, and it struggled from the beginning to secure a solid fanbase. Although the show was canceled after just two seasons, the roots for Sorkin's subsequent masterpiece - "The West Wing" (NBC, 1999-2006) - could easily be traced to "Sports Night," including his patented "walk and talk" technique and rapid-fire dialogue. In 2000, the cast was nominated for a Screen Actors Guild Ensemble Acting award, and Charles was singled out for a Best Actor Viewers for Quality Television Award nomination. Like "Sports Night," Charles as an actor was highly regarded, but flew under the radar compared to peers who were perhaps less deserving. The fact that the show was so beloved by critics and also so short-lived only added to its legend, and Charles's integral role in it gave his own reputation an impressive sheen.

For the most part, Charles kept a low celebrity profile, and his relationships were never the stuff of tabloid magazine covers. Charles's closest run-in with notoriety came when his two-year relationship with actress Jennifer Connelly ended amidst rumors that she had left him for her "A Beautiful Mind" (2001) co-star Paul Bettany. Although the principals kept tight-lipped about the situation, the media - albeit quietly - attempted to pry for details. Instead, Charles continued to work, notching another success with the award-winning "Our America" (Showtime, 2002), the real-life story of two African-American teens from the Chicago ghetto who win a contest held by a producer (Charles) to create a documentary about their lives and community. Back at the multiplexes, "S.W.A.T." (2003), based on the 1970s TV show, offered none of the uplift or power of "Our America," but entertained popcorn-munchers with lots of dumb-but-fun action. Charles played T.J. McCabe, a supporting member of the elite team which included Colin Farrell, LL Cool J, Michelle Rodriguez and Samuel L. Jackson.

Charles strapped on a badge again to play a detective whose investigation into a murder is complicated by the vigilante acts of "Four Brothers" (2005), the slain woman's adopted sons (Mark Walberg, Tyrese Gibson, Andre Benjamin and Garrett Hedlund). Loosely based on the classic Western "The Sons of Katie Elder" (1965), the urban action flick was a sleeper hit, and Charles was able to stretch a little as a crooked cop. He continued to line up small roles, often of the thankless variety, with audiences avoiding oddities like "The Darwin Awards" (2006) and "The Ex" (2006). Television again provided him with a better showcase for his talent, and he memorably recurred on dramas like "Six Degrees" (ABC, 2006-07) and "In Treatment" (HBO, 2008- ). The latter provided especially rich material, with Jake (Charles) and Amy (Embeth Davidtz) seeking couples' counseling from Dr. Paul Weston (Gabriel Byrne) - first to decide whether or not to have an abortion, and then whether or not to attempt to salvage their vicious and painful marriage.

Ever since his beginnings at Stagedoor Manor Theater Camp, Charles maintained a passion for stage acting, and over his career consistently appeared in countless productions, including Caryl Churchill's "A Number," Richard Greenberg's "The Well Appointed Room," Adam Bock's "The Receptionist," and Neil LaBute's "The Distance From Here." Charles still appeared in films, including John Krasinski's David Foster Wallace-inspired "Brief Interviews with Hideous Men" (2009) and the Christina Ricci undead thriller "After.Life" (2010), but television continued to claim the majority of his professional attention, and he scored an enormous success with "The Good Wife" (CBS, 2009- ). The show told the story of Alicia Florrick (Julianna Margulies), the wife of a disgraced state's attorney (Chris Noth) who must rebuild her legal career and life in the wake of her husband's scandal and incarceration. Charles played ace lawyer Will Gardner, an old friend of Florrick's who is still very much in love with her and must fight his feelings as they work together. Considered by many critics to be the best new show of the 2009 season, "Wife" earned excellent reviews and ratings as well as a loyal fanbase eager to see Charles's and Margulies's characters finally consummate their star-crossed love. For his work, Charles earned a Best Actor Satellite Award nomination and a Screen Actors Guild Ensemble Award Acting nomination, as well as a coveted Emmy Award nod for Outstanding Supporting Actor in 2011.

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