I think we could add Kris Kristofferson, Jerry Jeff Walker, Steve Earle, and John Prine to that list.
Those guys are all fine songwriters, but none of them sing worth a damn, IMO.
I’d add Leonard Cohen to the list of singer-songwriters with wonderful lyrics and mediocre-to-bad voices. But I love Tom Waits!
De gustibus and all that, but I would place Dylan, Cohen, and Waits on a list of performers where the cracked voice is an indispensible part of the experience, and covers by singers with more conventionally beautiful voices almost inevitably come off as superficial and inauthentic. (That “almost” is there mainly as a concession to fans of Jeff Buckley’s “Hallelujah.”)
Anyone who prefers their Waits smoothed out deserves the Eagles. 
Why not start with other artists versions of his stuff. Then, when your friend figures out what a good songwriter Waits is, he’ll start to listen to the real thing.
My best success with intro-ing folks to Waits;
Rosie (Beat Farmers)
Looking for the Heart of Saturday Night and San Diego Serenade (Dion)
Going Home with a Jersey Girl (Springsteen)
With all the other grating-voiced singers I get where you’re all coming from, but for Mr Waits, I believe it’s necessary that he sounds like he’s drunk a bottle of Redeye and smoked three packs a day since childhood. To me, that persona informs the songs. Like I would never imagine of the narrator of a Bukowski novel to have a voice like Julie Andrews.
As suggested above…
Get your friend a little inebriated…late in the evening.
Then expose him to an early beat poet version of Waits.
I vote for “Nighthawks at the Diner.”
According to Wikipedia, Waits’ voice was once described as sounding “like it was soaked in a vat of bourbon, left hanging in the smokehouse for a few months and then taken outside and run over with a car.”
I don’t yet know enough about Waits to make too many specific recommendations, but “Hoist That Rag” is an awesome song. Real Gone was actually the first album I bought, although I had heard a couple of songs from Blood Money before that. I have a few other albums now, but I think I like his later work a little better.
Me too. I think Real Gone is my second-favorite Waits, after Swordfishtrombones. And “Hoist That Rag” is an awesome song. Shivers.
Has anyone mentioned Dan Bern? 
When you sing about aliens having sex with monkeys and kind of finding your sister sexy and being the messiah, having a little unconventional singing voice actually adds to the experience.
[QUOTE=jackdavinci]
Has anyone mentioned Dan Bern?
Crash Test Dummies also comes to mind. But I forgot to answer the OP. Unfortunately I can’t help too much because I mostly used to listen to Tom when my coworker would bring in his CDs and I don’t have any of my own besides Night On Earth, which is a soundtrack so not as representative (and much of it is instrumental). Anyway I think the problem is less about which song you play and more about the fact that he doesn’t have a conventionally pleasing voice. I would make two suggestions:
-
Maybe watch Night on Earth the film. Hearing some of his stuff in the context of a movie may make it more emotionally relevant and also help distract his brain from preconceived notions about music since it’s a different context.
-
Try through reasoning or allusions to explain about music and singing that is enjoyable outside of strict conventions. For example, a person could enjoy an independant experimental film even though it doesn’t follow the conventions of a hollywood film. Or, for example, someone that is conventionally unattractive in real life you may avoid for fear of being hit on, but someone that is unusual looking in a sci-fi film might be considered attractive in the context of the film because of their exoticness. Most alcoholic beverages are technically not good tasting by conventional standards of thirst quenchingness, but still many people appreciate the interesting accompanying flavors in beer or wine, or the inherent bite of the alcohol itself in stronger drinks. If he’s a Trekkie, just say it’s Klingon opera. Every thing is context. Even if Tom Wait’s voice is not conventionally attractive, it’s interesting, and it’s fun, and it can definitely be enjoyable.
Stay out drinking way too long with your friend, then when you’ve talked to much about shitty times and everything feels raw, play “Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)”. If he doesn’t get it then, he never will.
I think it’s a bit harsh to refer to someone who doesn’t enjoy the warbling drunken weirdo pseudo-poetry of a gravelly voiced out-of-tune freaky looking urban cowboy, as an idiot.
Perhaps he simply doesn’t enjoy that kind of stuff.
All three of those folks sing perfectly well in the blues tradition of which they are a part. Plenty of people find their singing engaging and evocative, if not exactly mellifluous. Then again, mellifluousness just isn’t an aesthetic goal of theirs. Ever hear country blues? Hell, Charlie Patton makes those three sound like the three tenors, and I’ll fight the man who says he’s anything less than great.
Here’s how you make The Eagles:
Take The Byrds’ Sweetheart of the Rodeo, carefully remove Gram Parsons and replace with John Denver. Stir gently until smooth and allow to congeal. Serve lukewarm (serves millions).
[QUOTE=jackdavinci]
If he’s into Primus, point out that Waits and Les Claypool have collaborated on each other’s albums from time to time.
If he cannot be convinced of the awesomeness of either Primus or Waits, he has no taste and should be avoided.