1. Daria (Daria)
    Being the cynical, anti-social painter was never so cool. P.S. Quinn and the fashion club totally sucked.
  2. Uncle Jesse (Full House)
    The Elvis loving, hunky uncle with the best hair. Everyone wanted to be "Jessie's Girl."
  3. Zack Morris (Saved by the Bell)
    The dreamiest prankster at Bayside High and The Max. Not many Lisa Frank notebooks were left unbranded by his name.
  4. Donna Martin (90210)
    One of the fashionable "it" girls in the 90210 zip code. She proved you can be popular and still have your v-card.
  5. Kelly Bundy (Married... with Children)
    The trashy blonde slut. However, she would have kicked your ass, then stolen your boyfriend.
  6. Daniel Desario (Freaks and Geeks)
    The underdog stoner freak who no one could resist.
  7. Buffy (Buffy the Vampire Slayer)
    Not your average sexy cheerleader. What other high schooler had the gumption to kill vampires and date one?
  8. Kimberly, Pink Power Ranger (Power Rangers)
  9. Angela Chase (My So Called Life)
    The 'real' voice of teenagers in the grunge era + life lessons such as what time to sneak out at night.
  10. Dawson Leery (Dawson's Creek)
    Arguably the coolest or the worst. You pick.
  11. Bailey (Party of Five)
    I named my cat after him. My friends and j spent physics class wetting long plots of how Scott Wolf would fall in love with us and swoop us away from our miserable suburban lives.
    Suggested by @sarabethrubin
  12. Tia & Tamera Landry (Sister, Sister)
    Suggested by @anasha
  13. Alex Mack!
    Suggested by @supercommonname
  14. Topanga! See also: Shawn Hunter
    Suggested by @spiffypop
  15. Dylan McKay (90210) - coolest ever
    Suggested by @thelistyone
  16. Stefan Urquelle
    You know, Steve Urkel's alter ego. The. Coolest.
    Suggested by @jeffpdx