79 Bar Jokes: The 1999 “Party Like It’s 1999 & Y2K Panic” Edition

In 1999, every night at the bar felt like the last night on Earth. The atmosphere was a mix of futuristic excitement and “tech-pocalypse” dread. People were spending their savings on Blue Hawaiians and Apple Martinis, while bartenders were being asked if the electronic cash registers would explode at midnight. It was the year of The Matrix, Fight Club, and the birth of Napster—everyone was connected, but everyone was also a little bit paranoid.

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

1. The Y2K Cocktail: A guy asks for a “Y2K Special.” The bartender hands him a glass of water and a candle. The guy asks, “What’s this?” The bartender says, “A glimpse into your future on January 1st.”
2. The Matrix Choice: A bartender offers a guy two drinks: a blue shot and a red shot. The guy says, “If I take the red one, will I see how deep the rabbit hole goes?” The bartender says, “No, but you’ll see why we don’t clean the pipes often.”
3. The Napster Joke: A guy walks into a bar, takes a sip of someone else’s beer, and walks out. The bartender yells, “Hey!” The guy says, “It’s okay, I’m just ‘sharing’ it like Napster.”
4. The Prince Fan: A guy walks in and starts singing “Party like it’s 1999!” The bartender says, “Pal, it is 1999. You’re just partying normally.”
5. The Nokia 3210: A guy drops his Nokia 3210 in the bar. It cracks the floor tile. The bartender says, “That’s coming out of your tab, and I’m calling the demolition crew.”
6. The Internet Startup: A guy walks in and says, “I’m starting a website that delivers single ice cubes to your door.” The bartender asks, “Is it profitable?” The guy says, “No, but I just got 10 million in VC funding.”
7. The Millennium Martini: A guy orders a Martini with three olives. He says, “One for 1997, one for 1998, and one for the end of the world.”
8. The Red Bull & Vodka: A guy drinks five Vodka Red Bulls and says, “I can see the code in the Matrix!” The bartender says, “No, you’re just staring at the barcode on the bottle of Smirnoff.”
9. The Survivalist: A guy walks into a bar with 40 gallons of bottled water. The bartender says, “We have a sink, you know.” The guy whispers, “Not in three months, you won’t.”
10. The Britney Fan: A guy orders a shot and says, “Oops, I did it again.” The bartender says, “Yeah, that’s your fourth one. I’m cutting you off.”

The Full 1999 Bar Archive (Extended List)

11. The Apple Martini: A guy orders an Appletini. The bartender says, “One drink for people who miss elementary school snacks.”
12. The Blue Millennium: Why was the cocktail blue? Because it was worried about the 1st of January.
13. The Dial-Up Sound: A guy makes a screeching noise at the bar. The bartender asks, “Are you okay?” The guy says, “I’m just trying to connect to the conversation.”
14. The Flat Screen: A bar gets its first flat-screen TV. A guy asks, “Where is the rest of it?”
15. The Tequila Slammer: A guy slams a tequila and screams, “Y2K is coming!” The bartender says, “Your hangover is coming much sooner.”
16. The Cosmopolitan Queen: A woman orders a Cosmo and says, “I’m looking for my Mr. Big.” The bartender says, “The guy in the bathrobe at the end of the bar? That’s Mr. Big…ly Drunk.”
17. The Jägerbomb: The first Jägerbomb of the night is dropped. Somewhere, a computer programmer loses his wings.
18. The Pager’s Death: A guy throws his pager into his beer. The bartender asks, “Why?” The guy says, “If it doesn’t work in 2000, it’s dead to me now.”
19. The Screwdriver 2.0: A guy orders a Screwdriver and asks for “more megabytes of orange juice.”
20. The Fight Club: Two guys start fighting in the bar. The bartender says, “Rule number one: You don’t talk about the bar bill.”
21. The Star Wars Fan: A guy walks in dressed as Jar Jar Binks. The bartender says, “I have a bad feeling about this.”
22. The Liquid Assets: A guy tries to pay with stock options from an internet company. The bartender says, “I only take things that actually exist, like paper money.”
23. The White Russian: The “Dude” era continues, but now everyone is wearing pajamas to the bar. The bartender asks, “Is it laundry day or 1999?”
24. The Frosted Tips: A guy with frosted tips walks into a bar. The bartender asks, “Did you get stuck in a blizzard or is that just bad fashion?”
25. The Long Island Iced Tea: A guy says, “Make it strong enough to survive a power grid failure.”
26. The Bouncer’s Y2K Plan: “I’m not checking IDs on Jan 1st. If the world ends, we’re all 21.”
27. The Mojito: The Mojito starts becoming trendy. A guy asks, “Why is there a salad in my rum?”
28. The Champagne: A guy buys a bottle of Dom Perignon for New Year’s Eve 1999. He pays with a credit card and says, “Joke’s on you, this card won’t work tomorrow!”
29. The Gin Rickey: An old man orders a Gin Rickey. The bartender says, “A classic for the end of an era.”
30. The Heineken: A guy orders a Heineken and says, “The green bottle matches my night-vision goggles.”
31. The Corona: A guy asks for a Corona and two limes. The bartender asks, “Why two?” The guy says, “One for me, one for my bunker.”
32. The Budweiser Frogs: A guy walks in and says, “Bud… Weis… Er.” The bartender says, “I’m not a frog, and that joke is three years old.”
33. The Absolut Citron: A guy asks for Absolut Citron. The bartender says, “A zesty way to face the apocalypse.”
34. The Zima: The bartender finally throws out the last bottle of Zima. “Goodbye, 90s,” he whispers.
35. The Bourbon: A guy orders a bourbon and says, “Keep them coming until the clocks hit zero.”
36. The Guinness: Why does a Guinness take so long to pour? Because it’s waiting for the New Millennium.
37. The Shot Glass: A shot glass says, “I’m the only thing that won’t crash at midnight.”
38. The Cocktail Umbrella: A guy uses his cocktail umbrella to shield himself from the “digital rain.”
39. The Tab: A guy says, “Put it on my tab, I’ll pay you in the next century.”
40. The Bar Mirror: A guy looks in the mirror and says, “I haven’t aged a bit since 1900.” The bartender says, “That’s the spirit, Gramps.”
41. The Black Russian: A guy orders a Black Russian and says, “Like the screen of my computer when Y2K hits.”
42. The Mudslide: A guy orders a Mudslide and asks for an extra straw “for the journey.”
43. The Pina Colada: A guy orders one and says, “If the world ends, I want to taste like a vacation.”
44. The Strawberry Daiquiri: A guy orders one and asks the bartender to “make it look manly.” The bartender puts a plastic sword in it.
45. The Whiskey Sour: A guy orders a Whiskey Sour and complains about the price. The bartender says, “Inflation is a 20th-century problem.”
46. The Manhattan: A guy orders a Manhattan and says, “I want to be a part of it… before it’s gone.”
47. The Old Fashioned: A guy orders an Old Fashioned and says, “I’m staying in the 1800s. It’s safer there.”
48. The Sidecar: A guy orders a Sidecar and asks if it has an airbag.
49. The Rusty Nail: A guy orders a Rusty Nail and says, “It matches the plumbing in my fallout shelter.”
50. The Dark and Stormy: A guy orders one and says, “That’s the forecast for Jan 1st.”
51. The Sex on the Beach: A guy orders one and the bartender says, “Keep it in the glass, pal.”
52. The Kamikaze: A guy orders a round and says, “To the end of the world!” Everyone cheers.
53. The B-52: A guy orders a B-52 and says, “Let’s hope we don’t see the real ones tomorrow.”
54. The Lemon Drop: A guy orders a Lemon Drop and says, “A sour end to a sour decade.”
55. The Bloody Mary: A guy orders one and says, “I need the vitamins for the trek to the mountains.”
56. The Mimosa: A guy orders a Mimosa and says, “I’m practicing for the first brunch of the year 2000.”
57. The Sangria: A guy orders a pitcher and says, “It’s communal, like we’ll all be soon.”
58. The Margarita: A guy asks for a Margarita “with extra salt to preserve my nerves.”
59. The Martini Shake: The bartender shakes a Martini so fast he creates a rift in time.
60. The Beer Flight: A guy orders a flight and says, “Take me to the moon!”
61. The Draft Beer: Why was the beer so excited? It was finally going to be “vintage.”
62. The Coaster: A guy writes his email address on a coaster. The bartender says, “What’s an ‘@’ sign?”
63. The Bar Snack: A guy asks for “Emergency Pretzels.”
64. The Ice Cube: An ice cube says, “I’m 100% Y2K compliant.”
65. The Bottle Opener: The bottle opener says, “I’m manual. I’ll be the king of the bar tomorrow.”
66. The Bar Stool: A guy says to the stool, “You’re the only thing I can trust not to glitch.”
67. The Neon Sign: The “Open” sign flickers. A guy screams, “IT’S STARTING!”
68. The Pager Part 2: A guy’s pager buzzes. He looks at it and it says “000000.” He faints.
69. The Karaoke: A guy sings “End of the World as We Know It.” He misses every note.
70. The Pool Table: A guy hits the 8-ball in. He says, “That’s it, the game is over. For everyone.”
71. The Bouncer: The bouncer tells a guy, “You’re too drunk for 1999.” The guy says, “Check me again in the 2000s.”
72. The Bartender’s Tip: “The best tip for 1999? Buy gold and drink silver.”
73. The Vodka Tonic: A guy orders a Vodka Tonic and says, “Clear drinks for clear thinkers.”
74. The Rum and Coke: A guy orders a Rum and Coke and asks for a “New Millenium” straw. It’s just a regular straw with glitter.
75. The Wine List: A guy asks for the “Fin de Siècle” wine. The bartender gives him the house red.
76. The Closing Time: The bartender yells, “Last call of the millennium!”
77. The Midnight Count: 10… 9… 8… A guy hides under the pool table.
78. The New Year’s Kiss: A guy tries to kiss the bartender. The bartender says, “My Y2K bug is that I don’t like you.”
79. The Aftermath: It’s Jan 1st, 2000. A guy walks into the bar. The lights are on. The computer works. He says, “I wasted $5,000 on canned beans for nothing. Give me a beer.”