1. RuPaul on Sabrina the Teenage Witch
2. Michelle Obama on iCarly
3. Larry David on Hannah Montana
4. Justin Bieber on CSI
5. Ginuwine on Parks and Rec singing Pony for Li’l Sebastian
R.I.P. Li’l Sebastian
6. Pablo Schreiber (Pornstache from OITNB) on It’s Always Sunny in Philadelphia
7. Britney Spears on Sabrina the Teenage Witch
This was extremely relevant to my interests in 1999.
8. Death Cab For Cutie on The OC
9. Cher on Will & Grace
10. Victoria Beckham on Ugly Betty
11. Aziz Ansari on Scrubs
12. Tegan and Sara on The L Word
This really had so much potential to be an iconic moment for many lesbians, but it was just really bizarre in the end. Like most of that show actually.
13. Paris Hilton in Supernatural
14. Victoria Justice on iCarly as Shelby Marx
This one makes zero sense because a number of years later, Miranda Cosgrove made an appearance on the show Victorious playing Carly from iCarly.
How did Carly from iCarly meet Victoria Justice in this role and not say “Hey you look exactly like Shelby Marx?” I’m sorry this one’s just been on my mind a lot over the years.
15. Molly Ringwald poking fun at her own career in Not Another Teen Movie
16. The Backstreet Boys on Sabrina the Teenage Witch
How the hell did Sabrina secure all of these huge guest appearances?
17. Michael Jackson on The Simpsons
This episode was incredibly confusing to me as a child. Was it really Michael Jackson? Was it just Homer’s imagination? Did they just get someone to do an impression of his voice?
He wasn’t credited at the end of the episode, but it was in fact him. Because of his contract he wasn’t even allowed to sing any of his songs on the show.
18. Lily Allen on Neighbours
