Join hosts Kris McPeak and Annie Pruitt as they countdown their top five favorite songs from the Billboard Hot 100 list of 1999 on this exciting episode of the Top Five Podcast. They dive into a year marked by a notable country music presence and share nostalgic personal anecdotes tied to hits from bands like Backstreet Boys, Sixpence None the Richer, Smash Mouth, Pearl Jam, and Matchbox 20. Discover lesser-known gems, discuss enduring classics, and enjoy some playful banter, all while reminiscing about a memorable year in music. Tune in for a fun, music-filled trip back to 1999! And a playlist? Yup, I got your playlist RIGHT HERE. 00:00 Welcome to the Top Five Podcast 00:43 Introducing the Billboard Top 100 Series 01:27 Diving into 1999's Billboard Top 100 02:59 Chris's Number Five Pick: Backstreet Boys 04:16 Annie's Number Five Pick: Sixpence None the Richer 06:38 Chris's Number Four Pick: Len 08:12 Annie's Number Four Pick: Smash Mouth 10:07 Chris's Number Three Pick: Red Hot Chili Peppers 11:57 Annie's Number Three Pick: Pearl Jam 13:53 Rediscovering Pearl Jam Through TV Shows 14:32 1999 Grammys: A Historic Year for Female Artists 15:40 Shania Twain's Impact on Country Music 18:11 Fastball: The Two-Hit Wonder 19:39 Honorable Mentions and Nostalgic Hits 22:38 Britney Spears: The Pop Icon of 1999 26:34 Matchbox 20: A Retrospective 28:53 Recap and Final Thoughts