Sheboygan Confidential
1998

This has come up before. I had a long-standing tradition with my old college roommate of following the annual announcement of the Academy Award nominations by convening as quickly as possible to engage in what we termed “instant Oscar predictions.” This was fine in college, but became more difficult as pesky adulthood cast us to different corners of our mutual home state. Of course, during many of those years I was always looking for an excuse to take a roadtrip and compile a new mix tape for the occasion. So another part of the tradition for me involved transferring some carefully chosen songs to a cassette and hitting the road.

The title of the tape honored one of the most nominated films of the year in question, tweaking it to recognize the unique destination I embarked to in order to meet my cinematic combatant.

SIDE ONE
GRANDPABOY, “Psychopharmacology”
I’ve whined about Paul Westerberg’s solo career previously out here in the electronic wilds, so I’ll try to avoid repeating that lament. Instead, I’ll note it only to contextualize the fleeting thrill I had when the former Replacements frontman first took on this odd persona given to sloppy, reckless rock’n’roll songs. Back then, it took some real hunting to get this e.p., somehow adding to the intoxicating sense that it was some sort of Hootenanny second coming.
5 CHINESE BROTHERS, “I Can See”
RICHARD BARONE, “Something Happens”
BEN FOLDS FIVE, “Emaline”
ANI DIFRANCO, “Gravel”
This is the version that showed up on Living in Clip. I clearly remember hearing it for the first time while driving in my car across West Madison, the kind people at WORT-FM living the righteous babe’s music a rare trip across broadcast airwaves.
BOB MOULD, “Brasilia Crossed with Trenton”
Clip from the “Meatball Court” segment on MEATBALL RADIO
This is a radio comedy show I was involved in nearly twenty years ago. Typing those last four words freaked me out a little bit, so I don’t think I can elaborate at this time.
LIVING COLOUR, “Type”
THE VENTS, “Colleen”
BRUCE SPRINGSTEEN, “Sherry Darling”
GEAR DADDIES, “Goodbye Marie”
JACKSON BROWNE, “Rosie”
We all thought we were pretty clever when we figured out that this song off of Running on Empty wasn’t the sweet little love song it superficially seemed to be, but was instead an ode to the dependability of masturbation. Given that, it was a little weird to hear it reworked into a sweet little song paying tribute to Marge on an episode of The Simpsons.
Clip involving mouthwash rolling behind the tub from MEATBALL RADIO
SONIC YOUTH, “Mildred Pierce”

SIDE TWO
FOO FIGHTERS, “Everlong”
BARENAKED LADIES, “Brian Wilson”
This is hardly the coolest one-two punch I could have used to kick off side two, but I do need to admit that both these songs still sounded pretty good to me when I listened to the tape in preparation for this post.
THEY MIGHT BE GIANTS, “They’ll Need a Crane”
JONATHAN RICHMAN, “Let Her Go Into the Darkness”
I often made half-hearted attempts to include music that had been featured in films from the prior year when I made these particular tapes, and my first thought when listening back was that this must have been included because of its conspicuous use in There’s Something About Mary, but that was still a few months away from release at the time. The version used her comes from the live compilation culled from Conan O’Brien show performances so it may have been as simple as me wanted to use the coolest track from that relatively recent acquisition.
Clip from MEATBALL RADIO asking “How’d you like to wake up next to Keith Richards?”
ROLLING STONES, “Dead Flowers”
See what I did there? I’m ever so smart.
BEN LEE, “My Drifting Nature”
VICTORIA WILLIAMS, “Train Song (Demise of the Caboose)”
There’s a very brief portion of this song that sounds so much like a long lost Schoolhouse Rock song that it always seemed mildly unfortunate to me that Victoria Williams wasn’t enlisted to revive those animated bumpers.
BILLY JOEL, “Worse Comes to Worst”
JEN TRYNIN, “Love Letter”
Clip from the “Amish Motocross” sketch on MEATBALL RADIO
R.E.M., “Second Guessing”
For a time back then, I dependably went through a Reckoning phase every few months.
THE SILENCERS, “Razor Blades of Love”
VAN MORRISON, “Tupelo Honey”

Posted simultaneously to “Jelly-Town!”)