This week we keep things intentionally low-effort and high-chaos by drafting the Billboard year-end #1 songs from 1980 through 1999. We each build a ten-song playlist from a shared pool, knowing that once a song is picked, it’s gone forever. Along the way we uncover timeless masterpieces, generational blind spots, slow-dance trauma, and more than a few baffling chart decisions. By the end, it’s less about “best songs of all time” and more about what pop culture we survived — and what it says about the decades that made us.

Cold Open & Life Updates

• Eden survives Iowa weather whiplash, including snowmelt, wind advisories, and dogs who refuse to come inside.
• We check in on end-of-year fatigue, weddings on the horizon, and the general desire to just get to January.

What We’ve Been Checking Out

• Eden scores a surprise manga haul via Reddit, including:
  • Kase-san and… — a quiet, funny, wholesome romance that desperately wants its characters to communicate.
  • Chainsmoker Cat — gross, chaotic, and deeply committed to depicting the world’s worst anthropomorphic cat girl.
• Continued time in Where Winds Meet, including discovering that joining the “hot evil people” sect requires in-game marriage… followed by divorce.
• Peter continues slowly working through The Three-Body Problem and Gödel, Escher, Bach.
• A brief dive into habit-building via the new Atomic Habits workbook.
• Music check-in includes Archspire’s new single “Carrion Ladder” and the eternal joy of Apple Music Replay actually getting things right.
• Gaming includes Ball Pit, Megabonk, and the looming temptation of finally committing to Baldur’s Gate 3.

The Main Event: Billboard #1 Draft (1980–1999)

• We draft songs snake-style, locking each other out as we go.
• Early rounds are stacked with undeniable classics:
  • Whitney Houston’s “I Will Always Love You”
  • Prince’s “When Doves Cry”
  • Blondie’s “Call Me”
  • Cher’s “Believe”
• George Michael emerges as an ’80s powerhouse with multiple entries.
• The generational divide shows up fast:
  • Peter leans heavily ’80s.
  • Eden lives firmly in the ’90s (for better and worse).
• We acknowledge slow-dance staples that were emotionally formative whether we liked them or not.
• The middle rounds reveal just how strange pop history can be when viewed year-by-year.
• By the later picks, we’re openly throwing ourselves on grenades:
  • The Macarena is drafted out of mercy.
  • Multiple songs are chosen purely because something has to be.
• We question how certain cultural touchstones (My Heart Will Go On, Aaliyah, Bone Thugs) somehow missed the top spot in their years.

Big Takeaways

• Billboard #1 does not mean “best song.”
• The ’80s age better than the ’90s in pop memory (and fashion).
• Nostalgia is selective, and pop charts are cruel.
• Drafting music is a great way to discover what you genuinely love — and what you merely survived.