One word can send a playlist in a dozen directions. We set the rule to “May” and “might” and then let the songs do what great songs always do: open doors we didn’t expect. Jenn Tully fills in for Sam and joins Matt to trade picks that connect by title, lyric, and mood, and we keep the curation human, leaning on memory and instinct instead of outsourcing taste.

We start with the Bee Gees in their pre-disco glow, then jump to Led Zeppelin and the “May Queen” line that still feels like a life lesson about choices and changing course. From there, we test a common music debate: is “new country” actually bad, or did a certain pop-country era poison the well? Zach Bryan’s “Fifth of May” becomes the case study for modern country songwriting that feels specific, honest, and lived-in.

The ride keeps swerving in the best way. We talk Bruno Mars as a talent machine, Bruce Springsteen’s Nebraska era grit, and the hidden story inside the Goo Goo Dolls’ “Slide” when you actually listen to the lyrics. Then it’s The Cars, They Might Be Giants, and Metallica in a sequence that proves a good mix can handle whiplash if the theme is strong. We even slow down for “It Might Be You” and a real question about Tootsie, comedy, and whether nuance survives modern pop culture.

https://music.apple.com/us/playlist/may-might-songs/pl.u-4kK9uRm05v

1. First of May - Bee Gees
2. Stairway to Heaven - Led Zeppelin 
3. Fifth of May - Zach Bryan 
4. I Just Might - Bruno Mars
5. Atlantic City - Bruce Springsteen
6. Slide - The Goo Goo Dolls 
7. You Might Think - The Cars 
8. Birdhouse In Your Soul - They Might Be Giants 
9. Wherever I May Roam - Metallica 
10. It Might Be You - Stephen Bishop 
11. I May Be Used (But Baby I Aint Used Up) - Waylon Jennings 
12. May Ninth - Khruangbin

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