Update: I tried tracing this back to its origin, which I wasn't particularly successful at. The farthest back I was able to trace it was to a post made by 
princewien here. princewien got the idea from someone named Bryan, apparently, but I couldn't figure out who that was.
I think the first person I saw put together one of these lists was schwa242.
The game is:
Step 1: Open your MP3/media player.
Step 2: Put all of your music on random.
Step 3: List the first THIRTY songs it plays, no matter how embarrassing.
So here they are:
- Henry Thomas - Red River Blues
- Hal Willner - Weird Nightmare Interlude [from the Weird Nightmare: Meditations on Mingus album]
- Christopher Monti & Jacob Haller - Before You Accuse Me
- Clark Terry - Flugelin' The Blues
- 4'33" and the NeTe - Moscow Road Song
- Rudy Green - My Mumblin' Baby
- They Might Be Giants - Girls In Their Turning
- Tenacious D - The Road [fast]
- Mississippi Sheiks - Sitting On Top Of The World
- Hal Willner - What A Friend We Have In Jesus Revisited
- Lyle Lovett - I Loved You Yesterday
- The Killdevils - Johnny B. Goode
- Cal Tjader - Somewhere In The Night
- Christopher Monti & Jacob Haller - Bright Lights, Big City
- Charlie Parker, Buddy Rich, Flip Phillips et al -- The Afro-Cuban Jazz Suite
- Otis Redding - Security
- Olu Dara - Jungle Jay
- Hal Willner - Sango Montamaria
- Robert Johnson - Stop Breakin' Down Blues (Take 1)
- Johnny Shines - Too Wet To Plow
- Big Daddy - Welcome To The Jungle
- They Might Be Giants - Reprehensible
- Johnny Shines - Trouble's All I See
- John Coltrane - Naima (Alternate Take)
- Johnny Cash - Give My Love To Rose (w/June Carter)
- Christopher Monti, Jacob Haller, Gabe Luddy - Absolutely Legless
- The Nitty Gritty Dirt Band - Catfish John [f/Alison Krauss]
- The Nitty Gritty Dirt Band - Mama's Opry [f/Iris DeMent]
- Jelly Roll Morton - Original Jelly-Roll Blues
- They Might Be Giants - Concrete And Clay
So this is thirty songs chosen at random from the 4,179 I have in iTunes, for a combined playing time of ten days, seven hours, fifteen minutes, and thirty-four seconds, it says here. I need a bigger iPod.
A little commentary:
The most embarassing thing is probably the number of songs on my playlist that I actually recorded. Four out of thirty? Looking over my music collection, I see I do indeed have almost two hundred recordings of myself (usually with other musicians). Frightening.
I feel that it's a shame that only two of the thirty tracks are by women. Not even one freakin' Aretha Franklin or Memphis Minnie song? Gimme a break. I guess you live by the random playlist, you die by the random playlist.
Focusing more on the positive, Cal Tjader's a jazz vibrophone/percussionist who's really great and is worth checking out, Hal Willner's odd compilations take some getting used to but are also worth a listen, Big Daddy (a group that covers songs from the 60s up through present in the style of 50s musicians and groups) are far better than they have any right to be and are also highly recommended, and I love Olu Dara's From Natchez to Mississippi to pieces.