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The Roots were in Hollywood this past weekend for the 33rd Annual Playboy Jazz Festival, where the rap collective shared a stage with such jazz giants – and prominent hip hop sample sources – as Bob James, Harvey Mason and Fred Wesley.

Of course, the addition of a hip hop act had some jazz traditionalists tripping, but Roots drummer ?uestlove couldn’t be happier about the hate.

“There’s no situation in life that I love more than being underestimated,” he told EUR’s Lee Bailey ahead of the concert. “That’s been the story of The Roots. I feel like we’re ubiquitous and unknown at the same time.

“A lot of it has to do with the fact that in order to survive, we had to do gigs in places that you normally wouldn’t expect us to. So I think it challenges us to the point where we’ve made such a mark in the rock arena, and in the jazz arena – primarily doing hip hop and our brand of soul in these foreign arenas – that I’m almost more used to being in environments in which it might be a little head-scratchy as opposed to the environments that you would expect us to do.”

He continued: “If you were to say The Roots is gonna be in a show with Jill Scott, Erykah Badu and Maxwell, then I’d be a little nervous. You’d be like, ‘Well that’s your audience.’ But I’m like, ‘No.’ We’ve been planning on Plan B for so long, you know. Our life has been divided between opening for Soundgarden and The Duke Ellington Orchestra, and all stops in between the far left and the far right. To do something normal like that would almost seem foreign to us.”

?uestlove says he’s a collector of prominent moments in pop culture, including hundreds of “Soul Train” performances, and even Playboy Jazz footage of James Brown, Sly and the Family Stone and Stevie Wonder. But the time-keeper says his collection is missing some key radio memories that had a major influence on his childhood.

“I’m trying to get the history of RadioScope in one giant archive,” he said, after listing a number of vintage segments from Bailey’s syndicated program to prove how big of a fan he is.

“I’m talkin’ bout back when your listeners used to complain about Cameo having white women in the videos,” he began.

  • Continue ?uest’s trip down memory lane in the audio clip below; and watch The Roots rock “How I Got Over” at the 2011 Playboy Jazz Festival in the video clip.