Born Feb. 2, 1973 in New York City and raised in Bedford Village by her architect father and educator mother, Winokur's early years included stints on the cheerleading squad and captain of the soccer team at Fox Lane High School. Winokur began pursuing her theater dreams as a student in the integrated program at the American Musical and Dramatic Academy. By the early 1990s, she was making inroads on stage and on camera; a role in the national touring company of "Grease" in 1994 led to her casting as Pink Lady Jan in its 1995 Broadway incarnation. She was also able to log small but noticeable parts on "The Steve Harvey Show" (The WB, 1996-2002) and in features like the Drew Barrymore comedy "Never Been Kissed" (1999).
A bit part as a fast food counter girl who gets an earful from a stressed-out Kevin Spacey in "American Beauty" stuck in the memory of director Rob Marshall, who was involved in the early stages of a musical adaptation of cult director John Waters' most approachable film, "Hairspray" (1988). Marshall suggested that Winokur meet with him and the play's composer and lyricist, Marc Shaiman and Scott Wittman. The meeting convinced them that the young actress was right for the role of Tracy Turnblad, the show's spunky, civil rights-minded leading lady, but were hesitant to sign her without seeing other auditions as well. An agreement was struck between the production team and Winokur, which brought her on board to work with them, but stipulated that she could be replaced at a later date. After Winokur agreed to the proposal, disaster struck.
Winokur was diagnosed with cervical cancer. Terrified that she would lose the role of a lifetime if her condition was made public, she underwent treatment (including chemotherapy and a hysterectomy) and continued to work on the project. Only her family knew the true extent of her situation. Thankfully, her health improved over time, but another stumbling block presented itself; Marshall's participation in "Hairspray" was entirely dependent on the progress of a film version of "Chicago," and when that project was greenlit, he departed the stage musical and was replaced by Jack O'Brien ("The Full Monty") and choreographer Jerry Mitchell ("Legally Blonde: The Musical"). Winokur was told that she would need to audition for the role of Tracy, which would have put her up against hundreds of fellow actresses. However, her brassy vocals and comic and dance abilities also convinced the new team that she was born to play Tracy.
During the exhaustive pre-production phase of the play's inception, Winokur also kept busy with a host of guest shots on television and in film, including repeat appearances on "Dharma and Greg" (ABC, 1997-2002) and "Moesha" (UPN, 1996-2001). She also enjoyed a memorable cameo on "Curb Your Enthusiasm" (HBO, 2000- ) as a woman who tangles with Larry David over a doctor's appointment. But by 2002, Winokur's time was devoted almost exclusively to "Hairspray," which transferred from Seattle to Broadway in 2002. The production was a runaway success, winning eight Tony Awards and countless other Broadway laurels. Winokur herself brought home the Tony for Best Performance by a Leading Actress in a Musical, finding herself the toast of the Great White Way.
Following her huge win with "Hairspray," Winokur began landing more substantive parts on television. She was top-billed and served as executive producer for the ABC Family TV movie "Beautiful Girl" (2003), a breezy dramedy about a plus-sized teacher who enters a beauty contest to win money for her wedding. And in 2005, she made her debut as a series regular with "Stacked" (Fox, 2005-06), a short-lived comedy which cast her as an accident-prone employee at a bookstore that has hired a voluptuous new employee (Pamela Anderson). That same year, she contributed vocals to the song "Baby Face" for "Son of the Mask" (2005), and turned up in the Drew Barrymore/Jimmy Fallon baseball comedy Fever Pitch (2005), as well as several TV episodes. The following year, Winokur married Judah Miller, a former writer for "Stacked."
In 2007, Winokur was cast opposite Nikki Cox as identical twins for the comedy pilot "Fugly" (CBS, 2007). She also joined the original cinematic Tracy Turnblad's - Ricki Lake, and Nikki Blonsky - for the song "Mama, I'm a Big Girl Now" in the 2007 film version of the "Hairspray" musical. She also lent her voice to the TV holiday special "Shrek the Halls" (2007). The following year, she joined the sixth season cast of "Dancing with the Stars" (ABC, 2005- ) as one of its celebrity contestants. Although she was off to a rocky start, by the third week of the competition, Winokur was consistently picking up high scores from the judges panel. Despite being a fierce competitor, she was eventually knocked off the show in the semi-final round.
Winokur did, however, parlay her "Dancing with the Stars" experience into work as the host of the reality dance/weight loss competition, "Dance Your Ass Off" (Oxygen, 2009-2010). Moving on after one season, she was next seen as the "mother on the street" in segments of the daytime chat-fest, "The Talk" (CBS, 2010- ). This, too, lasted but a season when by mutual decision with the producers of "The Talk," Winokur left the show due to a lack of airtime. Beginning in its second season, the actress picked up a regular cast role on the sitcom "Retired at 35" (TV Land, 2011- ), as Amy, the successful sister of David Robbins (Johnathan McClain), a young man looking to drop out of the rat race and reconnect with his parents (George Segal and Jessica Walter) at their Florida retirement community.