Although the actor was nearing his mid-20s, he was cast in further high school-set projects, taking a recurring role on NBC's "Freaks and Geeks" and starring as a regular on The WB's "Popular". The latter featured Lester as Mike Bernadino, a high school student in the "in crowd" who was a school athlete as well as an aspiring rapper. Nicknamed 'Sugar Daddy', the character could be as sweet as his moniker suggested, but also had a mean streak, tormenting the have-nots when he felt insecure in his own social standing. Lester managed to keep the hip-hop wannabe character from becoming a farce, especially excelling in episodes that explored Sugar Daddy on an emotional plane. Situations like the character's expulsion from the wrestling team because of excess weight, his disappointment at being stood up by his partner in an Internet romance and his confusion over the battling affections of Nicole (Tammy Lynn Michaels) and Mary (Leslie Grossman) showcased Lester's abilities and won over the audience. In 2000, "Popular" won a Teen Choice Award and Lester's enthusiasm was among the more memorable moments in the televised ceremony.