Starring: Bill Hader, Seth Meyers
Aired: Oct. 23, 2010
Stefon is the most iconic character to come out of Saturday Night Live in the 21st century, and this specific appearance on "Weekend Update" is when he was at the peak of his powers. Every recurring SNL skit—even the classic ones—dies out the more it's rolled out. Just ask Kristen Wiig and every character she's ever done. This iteration of Stefon (there were 18 total) came early in his run though, when loyal viewers were just starting to beg for his appearances and the world of pop culture was just beginning to understand his stick. After this moment, Stefon became a phenomenon.
I can't say exactly what it is—the homeless robocops, Bark Ruffalo, Little Israel, or the fact that Bill Hader absolutely loses it when he mentions Sidney Applebaum, the Jewish Dracula. We all know Hader's thing is breaking character as Stefon—caused because SNL writer John Mulaney would change the jokes right before air—but this was on another level. The guy is actually crying. That's pure joy right there, and that's why Bill Hader has to be considered a Top 5 SNL cast member.