Jenna Dewan Recalls Early Career Days with Janet Jackson, Says Singer “Looked Out” for Her

Jenna Dewan is reflecting on her early days as a backup dancer for Janet Jackson, sharing personal stories about how the global pop star supported her at the start of her career.

Speaking recently, Dewan recalled joining Jackson’s All for You Tour in 2001 when she was just 18 or 19 years old. Because she was under the legal age for many venues the tour visited, Dewan said Jackson would sometimes step in to make sure she could still be included in group outings.

According to Dewan, Jackson took on a protective role, describing her as a “mama bear” who wanted her dancers close. She said Jackson would help her get into clubs and lounges so she wouldn’t be left out while the rest of the team spent time together.

Dewan also described a close bond with Jackson beyond the stage. She said they often spent downtime together, including casual hangouts in hotel rooms. “We were like homies,” Dewan said, recalling nights filled with laughter and relaxed moments during the tour.

One story that has stood out over the years involves a Valentine’s Day gift Jackson gave her dancers. Dewan previously shared on Jimmy Kimmel Live that Jackson handed out what she called a “pleasure chest,” a box of adult-themed items. Dewan said she was surprised by the gift at the time, describing herself as very naive early in her career.

Years later, Dewan experienced what she called a full-circle moment. In 2017, she joined Jackson on stage at the Hollywood Bowl for a special performance of “Rhythm Nation,” alongside other former dancers. She described the experience as one of the highlights of her life.

Dewan credits her time working with Jackson as a major stepping stone in her career. She said the experience helped prepare her for future opportunities, including her breakout role in the 2006 film Step Up.