Questlove reminisces about his famous hair, obsessions and his 20-year plus career

The Roots just crossed a massive milestone.

On October 24, while the band was rocking out onstage at Lipton's Be More Tea Festival in North Charleston, S.C., they were also celebrating the 20-year anniversary of the release of their hit record "Do You Want More?!!!??!"

"You know what's weird? It's like the tortoise and the hare. When you're actually active in running the race, you never turn around to see how far you've come. There's no instant replay that you can watch," Questlove revealed to AOL about the huge career landmark. "I'm afraid of jinxing it and saying something like 'Celebration!' I'm shocked that I have been able to get away with doing this for that long."

'Getting away with it' might be an understatement. The band, which technically started in 1987, has been churning out chart-toppers ever since.

In honor of the momentous occasion, we took a trip down memory lane with the hip-hop mogul to discuss some funny moments in 1995 -- the year everything really changed for him.

What was your biggest obsession in 1995?
That people don't know about? People that know me know that I am either about sneakers or records. My first advance, I went out and purchased 20 pairs of suede PUMAs -- every color. My favorite set was the traditional blue and grey. We went out tour with the Beastie Boys back then.

What was your biggest style obsession?
That's when I unveiled my afro to the world -- so a lot of relentless teasing. It took 5 years for the world to not sing a Jackson 5 song every time I walked into a room.

Biggest musical influences back then?
That's the year I first met J Dilla and I knew he was god then. Not like after he died. I knew probably the first day I met him that this guy was going to change my life. The fact that he even agreed to do work with me under the Soulquarians connection -- that was amazing. It was basically like Jesus and the disciples. I just watched him and I just knew that every moment was going to be a life changing, watching a genius at work.

What's one thing you wanted to accomplish back then that you may or may not have?
In hindsight, because of the competition back then, there were times where I'd be watching TV or look at Rolling Stone, or watch awards shows and think, 'I want my chance.' And we wouldn't get it. But like the tortoise and the hare, we got our just desserts now. All those groups that I was crying over back then, we're still here and most of them aren't. In hindsight, I'm glad that we didn't get that success back then because we would have been total arses.