My Coolest Years is a television program that aired on VH1 in which actors, musicians, and other celebrities reminisce about their high school years. Overview Past programs have centered on The Geeks, B-Boys and B-Girls, My Summer Vacation, In the Closet, Dirty Hippies, My First Time (sexual experience), Bad Girls, Jocks and Cheerleaders, Rich Kids, The Metalheads. Brian Kirk made his first TV appearance on this show. Celebrities interviewed include: Stephen Baldwin Tyson Beckford Nuno Bettencourt Jim Breuer Da Brat Nate Dogg Jermaine Dupri Fat Joe Christian Finnegan Andrew Firestone Warren G Vincent Gallo Kadeem Hardison Julio Iglesias Jr. Jordan Knight Juliette Lewis Angie Martinez Finesse Mitchell Kel Mitchell Steve-O O.A.R Catherine Oxenberg Paula Jai Parker Penn & Teller John Popper Rah Digga Sherri Shepherd Morgan Spurlock Sheryl Swoopes Ben Stein Joe Torry Rachel True Paul Tyma Wil Wheaton Andrew W.K. External links VH1 original programming 2004 American television series debuts 2005 American television series endings