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She also had starring roles in the CBS medical drama series City of Angels (2000) and in the films Cradle 2 the Grave (2003), Neo Ned (2005), Cadillac Records (2008), Top Five (2014), Breaking In (2018), and The Perfect Find (2023). She has also co-starred in the films The Birth of a Nation (2016), Almost Christmas (2016), and Sleepless (2017).

In high school, Union was an all-star point guard in basketball and a year-round athlete, also playing in soccer and running track. She went on to the University of Nebraska before moving on to Cuesta College. She eventually transferred to UCLA and earned a degree in sociology. While studying there, she interned at the Judith Fontaine Modeling & Talent Agency to earn extra academic credits. Invited by the agency's owner, Judith Fontaine, she started working as a model to pay off college loans.

Her career began in the 1990s, when she made dozens of appearances on TV sitcoms prior to landing supporting roles in 1999 teen films She's All That and 10 Things I Hate About You. She rose to greater prominence the following year, after she landed her breakthrough role in the teen film Bring It On. Bring It On helped push her into the mainstream and she began gaining more exposure. She was cast in her first leading role in the 2003 film Deliver Us from Eva with rapper L.L. Cool J. In 2003, she landed the role of Will Smith's girlfriend/Martin Lawrence's sister Sydney Burnett in the film Bad Boys II, and she starred with Academy Award winner Jamie Foxx in the film Breakin' All the Rules in 2004. She then starred in the short-lived 2005 ABC series Night Stalker. She has also starred in the independent drama films Neo Ned and Constellation, the latter of which was released to theaters. She won an award for Best Actress in Neo Ned at the Palm Beach International Film Festival, and the film received awards at several festivals.

Outside of acting, she has written four books: two memoirs, titled We're Going to Need More Wine (2017) and You Got Anything Stronger? (2021), and two children's books, titled Welcome to the Party (2020), and Shady Baby (2021).