In 5-4-3-2-1.
"La La" by Ashlee Simpson
Year aired: 2004
Why it's iconic: Ashlee Simpson before it all went to shit. For everyone who misses The Ashlee Simpson Show. She's 20 and playing emo in this video.
"Tainted Love" by Marilyn Mason
Year aired: 2002
Why it's iconic: It's Not Another Teen Movie with Marilyn Manson.
"Parents Just Don't Understand" by 3LW, Nick Cannon, and Lil' Romeo
Year aired: 2001
Why it's iconic: Everyone needs a little more 3LW. It's for the Jimmy Neutron soundtrack. Lil' Romeo is actually really lil. It's funny to watch him interact with adults around him because he is a child.
"I Learned From The Best" by Whitney Houston
Year aired: 1999
Why it's iconic: Whitney's only episode of Making The Video. It takes place in Germany. Bobby Brown: "We fight and we love but we love even harder." This episode is cryptic.