Dr. Horrible's Sing-Along Blog (2008)
It's probably the most high-profile Web series yet, and one of the best: Dr. Horrible's Sing-Along Blog was hatched by geek hero Joss Whedon (of Buffy the Vampire Slayer and Firefly fame) and stars Neil Patrick Harris, who's arguably been a geek hero for even longer--he was Doogie Howser, after all.
Self-funded by Whedon and created in conjunction with his two brothers during the Writer's Guild of America strike, the three-part Dr. Horrible is a campy musical about an aspiring supervillain (Harris) desperate to win over a girl (Felicia Day) while simultaneously conquering a superhero (Firefly's Nathan Fillion). Almost universally well-received, Dr. Horrible debuted this summer and is available on the iTunes Store and Web video hub Hulu.
Correction: This caption initially misstated the name of the actress Dr. Horrible is trying to win over. She's Felicia Day.
Photo by Dr. Horrible's Sing-Along Blog
Caption by Caroline McCarthy