Why was it a milestone? Because it was the night the old school (Santana) showed the new school (Britney, Backstreet Boys) that you can survive a millennium and still be the coolest person in the room—provided you have a guitar and a green Versace dress nearby.
Part of the 37 Grammy Jokes: The 2000 “Supernatural Santana & Christina’s Shock” Edition archive. Historically Verified
🔥 Top 10: The Grammy Awards Joke Archive: 1995–2025
2025 Legacy: Best Country Song
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2025 Vintage: Best Music Film
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Why did Kendrick Lamar win Record and Song of the Year? Because h...read more »
2025 Classic: Best Alternative Music Album
Why All Born Screaming? Because St. Vincent is the only person wh...read more »
2024 Archive: Best Progressive R&B Album
Why SOS? Because SZA turned a distress signal into a global celeb...read more »
38 Grammy Jokes: The 2010 “Single Ladies & Fearless Records” Edition
In 2010, the 52nd Grammy Awards were a battle of the titans. Beyo...read more »
40 Grammy Jokes: The 2020 “Bad Guy & The Eilish Takeover” Edition
In 2020, the 62nd Grammy Awards were a generational shift. Billie...read more »
39 Grammy Jokes: The 2015 “Stay With Me & The Beck Surprise” Edition
In 2015, the 57th Grammy Awards were a rollercoaster of British s...read more »
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In 1998, the 40th Grammy Awards felt like a fever dream. Bob Dyla...read more »
2024 Archive: Jay-Z’s Truth Bomb
Why did Jay-Z call out the Academy while holding a Dr. Dre Global...read more »
😜 More from category: The Grammy Awards Joke Archive: 1995–2025
2025 Legacy: Sabrina’s Espresso Shot
Why did "Espresso" win Best Pop Solo? Because Sabrina Carpenter b...read more »
38 Grammy Jokes: The 2024 “Midnights & Flowers” Edition
In 2024, the 66th Grammy Awards were a total takeover by women. I...read more »
35 Grammy Jokes: The 2017 “Adele’s Heartbreak & Lemonade Justice” Edition
In 2017, the 59th Grammy Awards were a showdown between two of th...read more »
37 Grammy Jokes: The 2000 “Supernatural Santana & Christina’s Shock” Edition
In 2000, the 42nd Grammy Awards were less about the future and mo...read more »
⏳ Time Capsule: This is how we rolled in the first two decades of the internet
Could this joke BE any funnier?
You got it, dude! Very funny.
Simply posh humor. I love it.
My goal is to not smile. I failed. This is funny.
I’m kind of a big deal. People know my jokes.
Searching for "humor"... HotBot never fails.
The layout of this joke is perfect. 10/10.