The "World of Dance" star reflects on touring with the pop icon while she was still in college.
"[Janet] was a great boss, she was a very generous boss. She would give us like amazing gifts," Dewan said. "I have a blinged-out diamond watch, which, by the way, should everything go away, I'm like, 'I could sell this watch!'"
"On Valentine's Day -- and mind you, I'm 19, on tour with Janet, so I'm like, baby, baby, baby naive -- she gives you, like, a box of vibrators," Dewan continued. "Like a pleasure chest. All the dancers [got a box]. But still, I was like, 'What is this?' I was mind blown."
"That's very thoughtful," Kimmel joked. "I would imagine that traveling with Janet Jackson has to be an experience unlike any other, like a first class type of thing."
"Yes," Dewan agreed. "I was in college, I was going to USC, so I went from like dorm life to being on private jets like right away. One time, we’re in rehearsal and we’re rehearsing for the 'All For You,' the HBO special and [Janet] comes in and she’s like, 'So, everybody pack your bags. We’re going to fly to Anguilla tomorrow and rehearse for two weeks. Everybody’s celebrating and I’m like 'Where’s Anguilla?'"
(For those asking the same question, it's a British territory in the Caribbean, east of Puerto Rico.)
Dewan continued, "We’d wake up, go out on to the beach, lay out, and rehearse from like two to seven -- and then go to the clubs. And then repeat for two weeks. That’s insane! Who does that?"
"Gosh, I wish I'd really learned to dance for Janet Jackson," Kimmel replied.
Same, Jimmy, same.
Being a dancer for Jackson was always Dewan's dream, so finding out that she booked the gig was a big (and slightly stressful) moment.
"I came out to L.A. I was going to college, and then I auditioned for her video," she recalled. "And then she came into the room one day, and was like, 'Um, everyone can leave. Jenna, can you stay?' And I was like, 'Uhhh, am I being fired? Like what's going on here?'She walks in, she was like, 'Do you wanna go on tour with me?' And I just freaked out. You know, that was my dream job."
The "Step Up" star is still super close with her idol and even had a "love fest" at Sunday's Billboard Music Awards, where Jackson gave a mind-blowing performance before being honored for her epic career.
"I went into her trailer. We have like a love fest ... She's mama, she called me her kid," Dewan said, which prompted Kimmel to circle back to the vibrator revelation: "She gave her kid vibrators?"
Dewan also joined "World of Dance" judges Derek Hough, Ne-Yo and Jennifer Lopez for an epic dance off for a promo for the new season of the reality show. The dancer absolutely killed it. Check out the video below.
"World of Dance" Season 2 premieres May 29th at 8/7c on NBC.