The pair made it the semi-finals but was eliminated 10th on November 16, 2020. On September 2, 2020, Jackson was announced as one of the celebrities competing on the 29th season of Dancing with the Stars, which premiered on September 14, 2020.
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Also in 2019, Jackson made her writing debut with the book Reach for the Skai: How to Inspire, Empower, and Clapback, and began voicing Summer on the Netflix animated series DreamWorks Dragons: Rescue Riders, which ended in 2020. The video gained worldwide popularity, and spawned a variety of memes due to her character being unable to escape the rapper. In 2019, Jackson was cast in the music video for Lil Nas X's " Panini". In 2018, Jackson made a guest appearance in Marvel Rising: Initiation as Glory Grant, a role she reprised in Marvel Rising: Chasing Ghosts, and Marvel Rising: Battle of the Bands. Following her success with Disney, Jackson promptly made a guest appearance in K.C. In 2016, Jackson was included on Time's list of Most Influential Teens, and in 2017, she received a nomination from the Shorty Awards for Best Influencer. Bunk'd premiered on July 31, 2015, and she departed from the series after its third season in 2018. In 2015, after Jessie ended, it was announced that Jackson would reprise her role as Zuri Ross in the Disney Channel series Bunk'd, a spin-off series. In 2013, she appeared as Joetta Watson in the Hallmark Channel television film The Watsons Go To Birmingham and in the year following guest-starred in an episode of Disney XD's animated series Ultimate Spider-Man. For the role, Jackson received an Image Award nomination. In 2011, she was cast as Zuri Ross in the Disney Channel sitcom Jessie, which aired from September 30, 2011, to October 16, 2015. She continued to make cameo and guest appearances in the television series Team Umizoomi, Royal Pains, and Boardwalk Empire, as well as the 2011 films Arthur and The Smurfs. In 2009, Jackson made a cameo in the film The Rebound, and in the same year was cast as a member of the Nickelodeon pre-school animated series Bubble Guppies, playing the role of Little Fish. Jackson's first major acting role was in the independent film Liberty Kid (2007), which was followed by a guest appearance in an episode of Rescue Me (2008).