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When she came to work as an intern, Judith Fontaine thought she was so pretty, she requested Union get some photos so the agency could book her as a model. Other earlier roles included teen movies such as 10 Things I Hate About You, She's All That, and Love & Basketball.She got the photos and Fontaine did book her as a model. In 1997, Union appeared in the sixth-season episode of Star Trek: Deep Space Nine—"Sons and Daughters" as the Klingon N'Garen.You’re in that room with every amazingly talented actress of every hue, and it's a dogfight, it's hard".She appeared in the ABC series Flash Forward alongside John Cho and Joseph Fiennes as Zoey Andata, a role for which she was nominated for an NAACP Image Award for Outstanding Supporting Actress in a Drama Series in 2010.Union has also addressed the shooting of Trayvon Martin and stated, "When you have influence I think it's the responsible thing to do, to speak out on an issue when you see injustice. we all should." Tanganyika Williams, the aunt of NBA player Matt Barnes, was killed on July 8, 2014.Union posted on both Instagram and Twitter, calling for anyone with information on the killer of Barnes's aunt to report their information to authorities.Union felt that she had been "blessed" with her role in the film, feeling it elevated her career.

Union related that every rape victim was "unique", which extended to how they believed justice should be carried out.

She also appeared in Sister, Sister as Vanessa, in Smart Guy as Denise, and in five episodes of 7th Heaven as Keesha Hamilton. In 2000 Union performed the role of Isis in the cheerleading movie Bring It On opposite Kirsten Dunst.

Bring It On helped push Union into the mainstream and she began gaining more exposure.

Union made an appearance in the 2007 Christmas film The Perfect Holiday, which opened on December 12.

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Since she had no children of her own, Union used her mother and sister to portray the divorced single mother of three in the film.

Union admitted that at the time of getting the script, she was turned off, but became interested after reading the script at her agent's insistence.