50. "La La" by Ashlee Simpson Year aired: 2004Why 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. 49. "Tainted Love" by Marilyn Mason Year aired: 2002Why it's iconic: It's Not Another Teen Movie with Marilyn Manson. 48. "Parents Just Don't Understand" by 3LW, Nick Cannon, and Lil Romeo Year aired: 2001Why it's iconic: Everyone needs a little more 3LW. It was 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. 47. "I Learned From the Best" by Whitney Houston Year aired: 1999Why 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. 46. "Underneath Your Clothes" by Shakira Year aired: 2003Why it's iconic: "It's not about sex. It's about love." Herb Ritts directed it. I could listen to Shakira describe things all day. 45. "I Keed" by Triumph the Insult Dog Year aired: 2003Why it's iconic: This is an episode devoted to a puppet. A PUPPET. 44. "Son of a Gun (I Betcha Think This Song Is About You)" by Janet Jackson Year aired: 2001Why it's iconic: Missy Elliott is in most of this episode. Janet Jackson with a baseball bat. 43. "Shape of My Heart" by The Backstreet Boys Year aired: 2000Why it's iconic: The only episode of Making the Video BSB ever did. AJ's beanie and purple-tinted sunglasses. 42. "Doesn't Really Matter" by Janet Jackson Year aired: 2000Why it's iconic: Joseph Kahn directed. Janet's first dancing video "in a while." 41. "Nobody Wants to Be Lonely" by Ricky Martin and Christina Aguilera Year aired: 2001Why it's iconic: There is a dove handler. Christina Aguilera's nose ring. 40. "Love Don't Cost a Thing" by Jennifer Lopez Year aired: 2000Why it's iconic: Jennifer Lopez falls on the beach. They blame the flip-flops. 39. "Hey Baby" by No Doubt Year aired: 2001Why it's iconic: Lots of awkward dancing. 38. "Don't Let Me Get Me" by Pink Year aired: 2002Why it's iconic: Autobiographical and dark AF. The burnt teddy bears are a metaphor for lost childhood. I feel like I really know her now. 37. "Ex-Girlfriend" by No Doubt Year aired: 2000Why it's iconic: This is Hype Williams' first time working with a "rock band." Gwen's pink hair. Fight scenes. Stunts. Braces? Pretty awkward because it's about Gwen and Tony's relationship even though they say it isn't (awkward). 36. "Always on Time" by Ja Rule and Ashanti Year aired: 2001Why it's iconic: Ashanti's debut! She's "up-and-coming talent." Ja Rule is "all about that." 35. "Come Clean" by Hillary Duff Year aired: 2002Why it's iconic: Hillary says the video is about showing the transformation from morning to afternoon. It never rains this much in California. 34. "All the Small Things" by Blink-182 Year aired: 1999Why it's iconic: Because it's the most iconic Blink 182 video. There's a real story arc in this episode. Nakedness. 33. "I Turn to You" by Christina Aguilera Year aired: 2000Why it's iconic: Christina Aguilera bragging about her Grammy win. Christina Aguilera can't stop talking about her Grammy win. Christina Aguilera talking about this song shows her in a whole new light. The first time her filming a video for a "real ballad." 32. "Pop" by NSYNC Year aired: 2001Why it's iconic: JC's hair. For some reason, MTV gave them cameras. Chris' facial hair. 31. "Without Me" by Eminem Year aired: 2002Why it's iconic: Joseph Kahn directed it. "Pretty much what people are used to seeing from Eminem." Dr. Dre. Eminem describes having Osama Bin Laden in his video as "trying to make light of a bad thing." 30. "The Hardest Part of Breaking Up" by 2GE+HER Year aired: 2000Why it's iconic: RIP Michael Cuccione (Jason "Q.T." McKnight). This is like a bonus episode of their TV show. The fact that there was a fake boy band that was even remotely popular is incredible and very telling of the time period. Like what? 29. "Escape" by Enrique Iglesias Year aired: 2001Why it's iconic: Anna Kournikova. Remember when they dated? "Escape" is one of Enrique's best. "Kiss her neck! Kiss her neck!" "No scratching. No biting." 28. "Fighter" by Christina Aguilera Year aired: 2003Why it's iconic: Christina Aguilera gets really deep when she is dressed up as a moth. 27. "Sk8er Boi" by Avril Lavigne Year aired: 2002Why it's iconic: The song is about her high school experience: "I used to skate in high school and I know what it feels like for people to look down on you." Avril trying to be relatable. Avril saying over and over again how she doesn't like to dress slutty. Her stylists: "We don't really dress Avril because Avril has her own style. We just help her." K. 26. "Rumors" by Lindsay Lohan Year aired: 2005Why it's iconic: The quintessential Lindsay Lohan music video. Lindsay says she's a dancer. The birdcage. She's orange. 25. "Confessions (Daughter to Father)" by Lindsay Lohan Year aired: 2005Why it's iconic: Right before shit hit the fan. Lindsay directed the video. Dina Lohan makes an appearance. Ali Lohan's debut. Pure, raw emotion. 24. "Crazy in Love" by Beyoncé Year aired: 2003Why it's iconic: Beyoncé acknowledges Kelly and Michelle's absence and says she's "sad" without them. Beyoncé pretends she isn't dating Jay Z. Dancing like she's never danced before. 23. "Rock Your Body" by Justin Timberlake Year aired: 2003Why it's iconic: Justin Timberlake's artsy fartsy video. Lots of lightbulbs. Lots of overexplaining of the lightbulbs. 22. "Like I Love You" by Justin Timberlake Year aired: 2002Why it's iconic: Justin's solo debut. He is 21. 7-Eleven. 21. "Lady Marmalade" by Christina Aguilera, Pink, Mya, and Lil Kim Year aired: 2001Why it's iconic: None of them know what the song means. It takes place in the 1940s (who knew?). Christina Aguilera's eyeshadow. 20. "Jenny From the Block" by Jennifer Lopez Year aired: 2002Why it's iconic: Peak Jennifer Lopez (as a pop star). BENNIFER. Ben's first music video. Jen constantly telling people she's the same Jen. 19. "Where You Are" by Jessica Simpson and Nick Lachey Year aired: 2000Why it's iconic: Newlyweds before Newlyweds. They seem happy. The carousel. Papa Joe being creepy. Leelee Sobieski and Chris Klein are in this video. 18. "I'm Not a Girl (Not Yet a Woman)" by Britney Spears Year aired: 2001Why it's iconic: Crossroads! This episode will give you anxiety. I still don't understand how this is a real place. She could have died. 17. "Survivor" by Destiny's Child Year aired: 2001Why it's iconic: It's so 2001. The inspiration is the show Survivor and Castaway. They made Michelle go in the water. 16. "The Real Slim Shady" by Eminem Year aired: 2000Why it's iconic: This was the time period where it was cool to diss Britney and NSYNC furthermore contributing to a culture of hate. So much bleach. Kathy Griffin's cameo. 15. "Come on Over" by Christina Aguilera Year aired: 2000Why it's iconic: Basically the most choreography Christina has ever done in a music video. The video concept is described as "very visual." She has to pick between three boys who have an "edge." Apparently they flew the confetti from the stairway dance scene in from Belize? It was a surprise. 14. "Me Against the Music" by Britney Spears and Madonna Year aired: 2003Why it's iconic: Britney says "believe it or not" this is the most choreography she's ever done in a music video. We find out Britney played Madonna the song during rehearsals for the VMAs, Madonna told her to make it her first single, and Britney asked her to sing on it. Madonna said OK. Britney describes Madonna as a "visual artist." 13. "Thong Song" by Sisqo Year aired: 2000Why it's iconic: Sisqo's silver head. Sisqo's pink-tinted sunglasses. This video took four days to film. For some reason, Andy Dick is in this episode. 12. "Heartbreaker" by Mariah Carey Year aired: 1999Why it's iconic: BIANCA. Also, the Mariah stand-in doesn't speak any English and gets really offended because everyone is laughing and throwing popcorn at her. 11. "It's Gonna Be Me" by NSYNC Year aired: 2000Why it's iconic: NSYNC gets turned into 10-inch dolls. Chris Kirkpatrick does a Mini-Me impression. 10. "Dirrty" by Christina Aguilera Year aired: 2002Why it's iconic: Leather chaps. The shower scene. She seems actually dirty. "I was never good at that America's sweetheart thing." Christina's Juggalette transformation moment. 9. "I'm a Slave 4 U" by Britney Spears Year aired: 2001Why it's iconic: The concept is abandoned Asian bathhouse club. DJ Skribble is there. Wade Robson. Britney flirting with Wade Robson. The orgy scene. Britney is afraid of lizards. 8. "Bootlylicious" by Destiny's Child Year aired: 2001Why it's iconic: Back when Destiny's Child seemed happy. It's Destiny's Child's 2001 homage to Michael Jackson in "Billie Jean." Styled by Tina Knowles. 7. "Waiting for Tonight" by Jennifer Lopez Year aired: 1999Why it's iconic: Jen describes the concept as like a millennium rave party in the jungle with a small city in the background. She gets burned by lasers. 6. "Stronger" by Britney Spears Year aired: 2000Why it's iconic: Britney says 18 was a really hard year for her. It's like no other choreography she's ever done before; she gets to be a "fierce Britney." The chair. Britney's first time working with Joseph Kahn. "One of the best director's I've ever worked with." 5. "Bye Bye Bye" by NSYNC Year aired: 2000Why it's iconic: Peak NSYNC. The most iconic NSYNC choreography. Justin's hair is funny. Lance says this is the first time the world is going to see a new NSYNC dance in two years (which is weird). There is a rotational room. They pretend to be puppets. 4. "Lucky" by Britney Spears Year aired: 2000Why it's iconic: Says she hates how celebrities say how depressing their lives are. "If you can't have fun then why are you doing it?" Describes director Dave Meyers as a "funny cookie." The first time she plays a character. Foreshadows her future. 3. "Toxic" by Britney Spears Year aired: 2004Why it's iconic: Her seventh (and last) episode of Making the Video. Joseph Kahn's finest work to date. Joseph thinks it's a big "if" that MTV approves it. Britney watches earlier episodes of her Making the Video. Britney says she's so strong and "looks like the Chyna wrestler." 2. "Oops!... I Did It Again" by Britney Spears Year aired: 2000Why it's iconic: Britney said she wanted to do a Mars-themed music video just because. The red catsuit. The hair. Britney checking out her hot guy slaves. The camera falling on her head. Nigel Dick. 1. "(You Drive Me) Crazy" by Britney Spears Year aired: 1999Why it's iconic: The second episode ever of Making the Video, more iconic than your faves. The concept of the video was her idea: "They're in a club and like dorky waitresses and they break out in dance because the song is strong and powerful." The choreography took four days to learn. Melissa Joan Hart's hair. She says this video will take her to the next level. Everyone's secret favorite Britney song.