Biography: Jen O'Brien is a pro skateboarder who became one of the first females ever to skate at the X Games and win a medal. She was the first to win TransWorld SKATEboarding’s Female Vert Skater of the Year award, became the first woman to skate in men’s vert doubles at X Games and was also the first action sports athlete to grace the cover of High Times magazine. O'Brien was inducted into the Skateboarding Hall of Fame in 2016.