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At age 15, she choreographed the video for "Ring the Alarm" by Beyoncé and signed a recording contract with the Neptunes' Star Trak Entertainment. During this period, Taylor appeared as a dancer in the video for Jay-Z's "Blue Magic"  and released her debut single, "Google Me." She earned wider recognition for work on Kanye West's "Dark Fantasy" and "Hell of a Life" from My Beautiful Dark Twisted Fantasy (2010).

In 2012, she signed with West's GOOD Music and appeared on the label's compilation album, Cruel Summer, which peaked at number two on the Billboard 200. Her debut studio album, VII (2014), topped the R&B/Hip-Hop Albums chart. Taylor starred in and co-choreographed "Fade" by Kanye West, earning the MTV Video Music Award for Best Choreography. She then released K.T.S.E. (2018), followed by The Album (2020), which entered the top ten on the Billboard 200 and featured collaborations with Missy Elliott and Lauryn Hill. Her fourth album, Escape Room(2025), received a Grammy Award nomination for Best R&B Album.

As an actress, Taylor appeared in films such as Stomp the Yard: Homecoming (2010) and Madea's Big Happy Family (2011) before taking on starring roles in Coming 2 America (2021) and The Rip (2026). She received critical acclaim for her portrayal of Inez in A Thousand and One (2023), earning the National Board of Review Award for Breakthrough Performance. For her performance in Paul Thomas Anderson's One Battle After Another (2025), she won the Golden Globe Award for Best Supporting Actress and received an Academy Award nomination. On television, she starred in the Ryan Murphy legal drama All's Fair (2025–present) and won an NAACP Image Award for her performance in the 2025 Netflix television film Straw.

Her other ventures include collaborations with Adidas and Air Jordan on limited-edition releases. Taylor has directed music videos for herself and other artists, and her feature directorial debut, Get Lite, starring actress Storm Reid, for Paramount Pictures.