36 Celebrity Jokes: The 1999 “Red Pill & Y2K” Edition

In 1999, we were convinced the world would end because of a computer glitch, but we were more worried about whether we should take the red pill or the blue pill. It was the year of leather trench coats, the return of the Jedi (with a very annoying sidekick), and a teenage pop explosion that made us all feel “Crazy.”

The 1999 Top 10: The “Matrix & Millennium Bug” Classics

1. Keanu Reeves (The Matrix): Why did Keanu start wearing sunglasses indoors? Because in 1999, it was the only way to hide the fact that he was actually just as confused about the plot as we were.
2. Britney Spears: Why was Britney the biggest star of 1999? Because she proved that if you wear pigtails and dance in a hallway, you can conquer the world faster than a Y2K bug.
3. George Lucas (The Phantom Menace): Why did fans wait in line for months? Because in 1999, we actually believed that a movie about trade disputes and a CGI frog-rabbit named Jar Jar Binks would be the greatest cinematic event in history.
4. The Y2K Bug: Why was 1999 the most stressful year for IT guys? Because they spent 12 months convincing us that our toasters would try to kill us at midnight on December 31st.
5. Ricky Martin: Why was everyone “Livin’ La Vida Loca”? Because in 1999, we realized that if you shake your hips enough, nobody cares if they don’t understand the rest of the lyrics.
6. Jennifer Aniston & Brad Pitt: Why was 1999 their peak? Because they were the only couple in Hollywood whose hair was more famous than their actual movies.
7. The Blair Witch Project: Why were we terrified of a pile of rocks? Because in 1999, we were still naive enough to believe that a blurry home video from a forest was a real documentary.
8. Christina Aguilera: Why did she want to be a “Genie in a Bottle”? Because in 1999, the only way to get a teenage girl’s attention was to promise her three wishes and a catchy pop hook.
9. Cher: Why was she still #1? Because “Believe” proved that if you use enough Auto-Tune, you can survive not only the 90s but the next three decades of pop culture.
10. The Sixth Sense: Why was Haley Joel Osment so tired? Because in 1999, seeing dead people was a full-time job, and Bruce Willis was the last person to find out he was on the shift.

The Full 1999 Celebrity Jokes Archive

11. Brendan Fraser (The Mummy): Why was he the king of 1999? Because he proved that running away from sand with a face on it was a legitimate career move.
12. The Backstreet Boys (Millennium): Why did they dress in all white? Because in 1999, they wanted to look like the angels who would save us from the impending digital apocalypse.
13. Eminem: Why did everyone’s parents hate 1999? Because a blond guy from Detroit named Slim Shady started telling kids exactly what he thought about their mothers.
14. American Pie: Why did we stop eating dessert? Because Jason Biggs made us realize that a warm apple pie was no longer just a tasty treat, but a social hazard.
15. Jennifer Lopez (On the 6): Why was she “Waiting for Tonight”? Because in 1999, J.Lo decided that being a movie star wasn’t enough; she needed to dominate the dance floor too.
16. Austin Powers (The Spy Who Shagged Me): Why was Mini-Me so popular? Because in 1999, we realized that the only thing funnier than Dr. Evil was a version of him that fit in a carry-on bag.
17. Shania Twain: Why did she feel like a woman? Because in 1999, leopard print and a “Man! I Feel Like a Woman!” anthem were the only things keeping country music on the pop charts.
18. Lou Bega: Why did he only need “Mambo No. 5”? Because in 1999, he managed to name-drop every girl in his phone book and turn it into a global dance craze.
19. The Red Hot Chili Peppers (Californication): Why did they go to the moon? Because in 1999, a CGI music video about a video game was the most “futuristic” thing we could imagine.
20. Adam Sandler (Big Daddy): Why was he raising a kid? Because in 1999, Hollywood decided that if a guy who shouts “Scuba Steve” can be a father, anyone can.
21. TLC (No Scrubs): Why did they hate “Scrubs”? Because in 1999, a guy hanging out the passenger side of his best friend’s ride was officially the lowest form of life.
22. Julia Roberts (Notting Hill): Why was she “just a girl, standing in front of a boy”? Because in 1999, we still believed that a billionaire movie star would fall for a guy who works in a travel bookstore.
23. Santana (Smooth): Why was Rob Thomas everywhere? Because in 1999, you couldn’t enter a shopping mall without hearing a Latin guitar riff and someone singing about the “ocean under the moon.”
24. The Sopranos: Why did we start rooting for the mob? Because in 1999, Tony Soprano proved that even a guy who kills people for a living needs a therapist and a bowl of pasta.
25. Fight Club: Why can’t I tell you this joke? Because the first rule of 1999 was that you do not talk about Brad Pitt’s six-pack.
26. NSYNC (Bye Bye Bye): Why were they puppets? Because in 1999, Justin Timberlake’s curls were the only thing actually pulling the strings of the music industry.
27. Hugh Grant: Why was he in Notting Hill? Because in 1999, he was the only man alive who could look that awkward and still get the girl and the box office record.
28. Blink-182: Why were they running naked through the streets? Because in 1999, pop-punk was about three things: power chords, jokes about your age, and not wearing pants.
29. Macy Gray: Why did she “try to say goodbye and she choked”? Because in 1999, her voice sounded like a beautiful rasp that we all tried—and failed—to imitate.
30. Star Wars (Darth Maul): Why did he have a double-bladed lightsaber? Because in 1999, one blade wasn’t enough to distract us from the fact that Anakin was just a kid who liked pods.
31. Dr. Dre & Snoop Dogg (Still D.R.E.): Why were they “Still”? Because in 1999, they wanted to remind everyone that they hadn’t changed, even if their bank accounts had grown five zeros.
32. The Iron Giant: Why were we crying over a robot? Because in 1999, Vin Diesel’s best role was a giant metal man who just wanted to be Superman.
33. Lance Armstrong: Why was everyone wearing yellow? Because in 1999, we started believing in miracles on a bicycle, unaware of the pharmacy involved.
34. Sugar Ray: Why was it “Every Morning”? Because Mark McGrath’s frosted tips were the only thing that rose faster than the sun in 1999.
35. The Virgin Suicides: Why was it so dreamy? Because Sofia Coppola proved that in 1999, being a sad teenager in the 70s was the ultimate aesthetic.
36. Prince: Why was he the busiest man on earth? Because he spent 17 years waiting for December 31st, 1999, just so he could finally say “I told you so.”