Created from a list by The Whelk, a user on Metafilter - https://www.metafilter.com/182361/Summer-Mix-1999-good-vibes-only
1 SpongeBob - Pizza Delivery 2 Britney Spears - Hit Me Baby One More Time 3 TLC - No Scrubs 4 Len - Steal My Sunshine 5 Will Smith - Miami 6 Lou Bega - Mambo No 5 7 MTV Music Awards - Armageddonsync 8 Backstreet Boys - I Want it that Way 9 Smash Mouth - All Star 10 Regis Philbin - Who wants to be a Millionaire 11 Ricky Martin - Livin' la Vida Loca 12 Robbie Williams - Millenium 13 Macy Gray - I Try 14 Filter - Take a Picture 15 Jennifer Lopez - If you had my Love 16 Sixth Sense - Trailer 17 Eminem - My Name is 18 The Matrix - Pills 19 Blink 182 - What's my Age Again 20 Charli XCX - Troye Sivan 1999 21 George Bush - Announcement