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.
