Guest roles on such forgettable series as "Wasteland" and the remade "Fantasy Island" (both ABC) and a starring turn as a high school diver whose girlfriend brings him warnings from beyond the grave in "Dying to Live" (UPN) paved the actor's way in 1999, a year he capped with a featured supporting role as a ne'er-do-well prep school student in the 1970s-set comedy "Outside Providence". Mann played the long-suffering boyfriend of both the virtuous Jody (Brittany Murphy) in "Cherry Falls" and Mena Suvari's "Live Virgin" in 2000 releases that fared well on video. He reached a wider audience as Alan M in "Josie and the Pussycats", his rumpled hipster take on the love interest of the lead singer (Rachael Leigh Cook) an update on the more athletic all-American Alan featured in the animated series source.

Mann had a challenging role as a rock journalist who must face the artist (Kim Dickens) whose personal torment he knows all too well in Alison Anders' "Things Behind the Sun", which premiered at the 2001 Sundance Film Festival but was aired on Showtime in lieu of a theatrical release. That same year, he supplied the only moments of emotional verity with a charming and memorable supporting turn as the hometown best friend of a pitcher (Freddie Prinze Jr.) headed for bigger things in the lackluster baseball feature "Summer Catch". Mann also was featured in "New Port South" (2001), a portrait of high school-set civil disobedience and continued to take role after varied role in such film festival-screened independents as "Sleep Easy, Hutch Rimes" (2000) and "Buffalo Soldiers" (2001), proving a chameleonic performer with a bright future.