Born on May 15, 1963 in Los Angeles, Heslov was raised in nearby Palos Verdes, where he attended high school and grew up desiring to become an actor. With diploma in hand, he attended the University of Southern California as a theater major and after graduating, soon began landing small but memorable roles in features like the Two Corey's (Haim and Feldman) teen comedy hit, License to Drive (1988), as well as roles in episodes of noted television shows, including "Happy Days" (ABC, 1974-1984), "Family Ties" (NBC, 1982-89), and "The Facts of Life" (NBC, 1979-1988). It was while working on "Facts of Life" that Heslov met George Clooney, who at the time was a regular on the show. Cast as a nebbish competitor with Clooney for the hand of Blair (Lisa Welchel), Heslov's guest spot on the 1986 episode, "The Reunion," was worth any future embarrassment, as he found a kindred spirit in the future megastar. The pair remained fast friends, thanks in part to Heslov loaning the future megastar $100 to pay for a set of headshots. As he continued landing guest spots on the small screen, including a prominent episode of "L.A. Law" (NBC, 1986-1994), Heslov was snagging parts in features like "Legal Eagles" (1986), "Sunset" (1988) and "Catch Me If You Can" (1989) - the latter of which gave him one of his first starring roles, albeit in a small independent that saw a limited theatrical release.
Heslov continued to land supporting roles in film and television over the next decade, logging episodes on many of the popular series of the 1990s, including "Murder, She Wrote" (CBS, 1984-1996), "21 Jump Street" (Fox, 1987-1991), "Baywatch" (syndicated, 1989-2001), "Seinfeld," (NBC, 1989-1998) and "thirtysomething" (ABC, 1987-1991). He also turned up in small, but amusing roles in several comedy features, including as code specialist Faisil in James Cameron's True Lies (1994), as a scandal sheet photographer in the Robin Williams comedy The Birdcage (1996), as a member of the United States Geological Survey in Dante's Peak (1997), as well as in "Enemy of the State" (1998). During this time, Heslov made his directorial debut with a charming short film, "Waiting for Woody" (1998), in which he also starred as a down-on-his-luck actor whose hopes for a continued career are pinned on a meeting with Woody Allen. The film won several festival prizes, including the New York International Independent Film and Video Award.
In 2000, George Clooney's box office and television clout was sizable enough for him to mount a live remake of "Fail Safe" on CBS, with Stephen Frears directing. Not surprisingly, the loyal Clooney cast Heslov in a supporting role. That same year, Clooney and Soderbergh founded a production company, Section Eight Entertainment, and Heslov was tapped as the president of its television division. Despite the responsibilities of his new position, Heslov managed to find time to appear in films and television, including appearances on "Yes, Dear" (CBS, 2000-06) and in an "X-Files" (Fox, 1993-2002) episode, which saw his character devoured alive by rats. His feature work during this period included the independent comedy Bug () and the CGI-laden action-adventure, The Scorpion King (2002). In 2002, Heslov stepped behind the camera to direct his first feature film, "Par 6," a comedy about a determined family trying to build a golf course in the desert, which he wrote and co-produced with his wife, Candice Levenson. Though it screened at the Newport International Film Festival in 2002, the film failed to gain a theatrical release.
Heslov followed by entering the producer game, co-producing the Coen Brothers' dark comedy about divorce and revenge, Intolerable Cruelty (2003), starring Clooney and Catherine Zeta-Jones. Next he helped oversee two short-lived HBO series - "K Street" (2003), a semi-fictional look at the underbelly of Washington politics as seen through the eyes of James Carville and Mary Matalin, and "Unscripted" (2004), a look at the lives of struggling actors in Hollywood. Though both shows were critically praised for their quality, neither lasted beyond their first seasons. Turning to features, Heslov and Clooney penned the script for "Good Night and Good Luck" (2004), a drama based on the battles waged between legendary newsman Edward R. Murrow (David Strathairn) and Senator Joseph McCarthy (seen in real stock footage) on live television during the latter's height of power in the 1950s. With Clooney directing and co-starring as "CBS News" producer Fred Friendly, Heslov served alongside Steven Soderbergh as one of the producers, while playing future "60 Minutes" producer Don Hewitt. Shot entirely in black-and-white, the film received considerable praise from critics and fans alike, while receiving six Academy Award nominations, including two for Heslov for Best Screenplay and Best Picture.
After serving as the Section Eight production executive on the supernatural misfire, "The Jacket" (2005), Heslov had a substantial supporting role in the pilot episode of "Sleeper Cell" (Showtime, 2005-07), playing a reluctant terrorist named Bobby Habib, who unwittingly helps an undercover FBI agent (Michael Ealy) infiltrate a terrorist group about to launch an attack in Los Angeles. When Section Eight shuttered its business, Heslov and Clooney went partners in their new production company, Smoke House, releasing their first feature, Leatherheads (2008), under the new banner. Directed by Clooney and set in 1925, "Leatherheads" was a look at the formation of professional football wrapped around a romantic comedy that featured Clooney and Renée Zellweger. Unfortunately, Smoke House's first producing venture received mixed critical reviews and disappointing box office numbers. Meanwhile, Heslov took his turn in the director's chair for the producing duo's next project, The Men Who Stare at Goats (2009), a dark military comedy based on the non-fiction book about a journalist (Ewan McGregor) investigating a top secret U.S. Army unit that explored paranormal methods to combat enemies, including trying to stop a goat's heart using telekinesis. Heslov followed up by co-writing and producing The Ides of March (2011), director Clooney's political drama about a up-and-coming press secretary (Ryan Gosling) for a presidential candidate (Clooney) who finds himself involved in a scandal. The film was widely praised by critics, as Heslov shared an Academy Award nomination for Best Adapted Screenplay with Clooney and playwright Beau Willimon.
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