6. Whassup! (Season 13, Episode 11 - The Bart Wants What It Wants)
https://youtu.be/GzJBoaOzMUo The plot for this episode sees Bart befriend Rainier Wolfcastle's daughter, Greta (Reese Witherspoon), and when Bart goes to her house, Milhouse jumps into frame, enthusiastically shouting "Whassup!" as a greeting, while Bart looks on embarrassed and Greta is disappointed that she doesn't have alone time with the object of her affection. It is, of course, a reference to the enormously popular Budweiser commercials which aired from 1999 to 2002, but the joke here is that, though Milhouse is using the quote in an effort to be cool and impress Greta, he's at least two years too late, considering that the whole "Whassup!" thing was cool in 2000, and this episode aired in 2002. Milhouse also uses the catchphrase again in the 2005 episode See Homer Run, but the original is the best.
Stay at home dad who spends as much time teaching his kids the merits of Martin Scorsese as possible (against the missus' wishes).
General video game, TV and film nut. Occasional sports fan. Full time loon.