When Asher Roth was 17, he remembered being a car-less "white boy wannabe."
The lively artist developed a fan base while attending college with the help of social-networking websites, and arrived on the mainstream hip-hop scene with a slew of mixtapes. Almost overnight, he found himself with a record deal and a full studio album, Asleep in the Bread Aisle.
"In high school, I ended up finding my home with kids who had one common interest, and that's hip-hop music," Roth said on the latest episode of "When I Was 17," which premiered Saturday at 11 a.m.
"We'd be carrying boom boxes around in our book bags like we were straight out of the '80s," Roth's friend Brian recalled. "We started meeting regularly around school."
Before hanging with Hef, former "Girl Next Door" Kendra Wilkinson remembers eyeing her high school soccer coach.
"Soccer was my love," the California girl said. "I had a huge crush on my soccer coach. He was like the hottest thing to ever exist ... I would totally flirt with him. I would wear shorter shorts than the other girls on purpose."
Holly Madison and Bridget Marquardt said Wilkinson would act like she didn't know what she was doing on the soccer field to get more attention from the studly coach. "I loved just having my soccer coach just yelling at me. It turned me on," Wilkinson said.
Kendra also reminisces about how she was freaked out when seeing windmills turning with no wind and hearing a crying baby at a cemetery.
MTV reality-show vet Kelly Osbourne looks back at her time in an American school and her first tattoo experience.
"For me, it's really the idea of having a tattoo than actually having it because once you have it, you're like, 'alright, ugly.'
Kelly's first impressions of the American school system were also unique.
"In England, I just went to school," she said. "In America, I had to figure out if I was a jock, a nerd, a cheerleader — there are social groups for everything."
"When I Was 17" airs Saturdays at 11 a.m. on MTV.