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Gary Winick earned his BA at Tufts University and his MFA from the University of Texas and the American Film Institute. Winick taught at NYU's Tisch School of the Arts for seven years, and in 1999 teamed up with John Sloss and IFC Productions to create Independent Digital Entertainment (InDigEnt) to produce digital video feature films to be released theatrically.

Winick's producing credits include: Final, directed by Campbell Scott; Chelsea Walls, directed by Ethan Hawke premiered in the Director's Fortnight at the 2001 Cannes Film Festival; Tape, directed by Richard Linklater and Women In Film, directed by Bruce Wagner premiered at the 2001 Sundance Film Festival; Ten Tiny Love Stories, directed by Rodrigo Garcia; Wake Up And Smell The Coffee, directed by Michael Rauch; Personal Velocity, directed by Rebecca Miller, premiered in the Dramatic Competition at the Sundance Film Festival in 2002 and won the Grand Jury Prize, the Cinematography Award, and also won the 2003 John Cassavetes Independent Spirit Award; Pieces of April, directed by Peter Hedges, premiered in the Dramatic Competition at the 2003 Sundance Film Festival, and Patricia Clarkson was nominated for a Golden Globe and an Academy Award for her role; Kill The Poor, directed by Alan Taylor; November, directed by Greg Harrison, premiered in the Dramatic Competition at the 2004 Sundance and won the Cinematography Award; Pizza, directed by Mark Christopher; Land Of Plenty, directed by Wim Wenders, premiered in the Dramatic Competition at the 2004 Venice Film Festival and won the UNESCO Award; Lonesome Jim, directed by Steve Buscemi, premiered in the Dramatic Competition at the 2005 Sundance Film Festival; Sorry, Haters, directed by Jeff Stanzler, premiered at the 2005 Toronto International Film Festival; Flakes, directed by Michael Lehmann; and Puccini For Beginners, directed by Maria Maggenti, premiered in the Dramatic Competition at the 2006 Sundance Film Festival.

Winick's film directing credits include Curfew (1988), Out of the Rain (1991), Sweet Nothing (1996), and The Tic Code, which won the Glass Bear at the 1999 Berlin Film Festival. Winick directed two digital feature films, Sam the Man (2000) and Tadpole, which premiered in the Dramatic Competition at the 2002 Sundance Film Festival and won the Best Director Award. Winick directed 13 Going On 30 (2004) for Revolution Studios.