Friday Five: Songs About Waitresses

Juli Thanki | June 5th, 2009

Kiss my grits; it’s a playlist about waitresses. From hash-slinging to, well, hash-slinging, these women have seen and done it all. Don’t boss ‘em, don’t cross ‘em, and for Pete’s sake, tip nicely.

  • Lucinda Williams/Robert Earl Keen 5. “The Night’s Too Long” – Lucinda Williams/”The Road Goes on Forever” – Robert Earl Keen
    Two waitresses escape their humdrum existence for something else. Williams’ Sylvia trades one monotony for another as she ends up working in an office for average pay; Keen’s Sherry winds up in Miami as the wheelman for some shady happenings, and then she shoots a cop. But all’s well that ends well, and Sherry ends very well with a new car and a whole lot of money. Her companion, on the other hand…well, that’s a story for another playlist.
  • Jypsi - Jypsi 4. “Halfway Home Café” – Jypsi
    The winsome family band ably tackles this song told from the perspective of a waitress who observes the daily happenings of released prisoners, adulterers and various other down-and-outs in between serving up coffee and burgers. There’s something intimate in dining, no matter the locale, and “Halfway Home Café” provides a tiny peek into these new worlds that not many of us are privy to–except, that is, in a good song.
  • John Berry - Greatest Hits 3. “She’s Taken a Shine” – John Berry
    The love of a good man turns dowdy diner waitress Rosie into a vivacious new woman. Rosie becomes “the woman that she’s never been,” and Jesse will probably never have to pay for another plate of cheese fries for the rest of his life. That, my friends, is what they call a win-win situation.
  • The Waifs - A Brief History... 2. “The Waitress” – The Waifs
    Australian Americana band gives us a look at a waitress in another hemisphere. Turns out she’s got the same problems as her stateside sisters: bills, boyfriends in touring bands and struggling music careers. Granted, when the Simpson sisters sing, “My songs don’t earn me money or fill my pockets with cash/Every time I go busking I earn more in hash,” they probably aren’t talking the same type of hash served up with greasy breakfast meat in Sylvia’s diner in Beaumont, but the world-weariness of both women is identical.
  • Freakwater - Old Paint 1. “Waitress Song” – Freakwater
    “Waitress Song,” from 1995’s Old Paint, showcases Freakwater at its very best: a solid alt-country arrangement combined with visceral songwriting. Sure it’s nice to imagine Sherry or Rosie escaping the monotony of their lives and beginning anew, but in real life, most folks end up like this unnamed waitress with the world on her shoulders, singing, “If I didn’t go to bed afraid about some bills that’ll never get paid/I wouldn’t be down at the Laundromat watchin’ my work clothes fade.”

Listen to this playlist on Rhapsody

  1. Paul W Dennis
    June 5, 2009 at 2:18 pm

    “Betty, I’m Singing Your Song” – Dave Dudley (approximately 1972) is about a truckstop waitress

    “Truck Driving Man” – Orville Couch (approximately 1962) later Buck Owens and many others references truckstop waitresses in its verses

  2. idlewildsouth
    June 5, 2009 at 2:18 pm

    I love Ricky Skaggs version of “Halfway Home Cafe”. Ill have to listen to theirs. Im a sucker for most anything Paul Overstreet.

  3. Nicolas
    June 5, 2009 at 3:24 pm

    I love the song “Sometimes Goodbye” by Terri Clark <3

  4. Rick
    June 5, 2009 at 3:51 pm

    Finally Jypsi earns a bit of well deserved praise at 9513! Miracles do still happen! (lol)

    I know the song is universally rejected at The 9513 as overly sentimental treacle, but Clay Walker’s “Chain of Love” does deserve to be part of this discussion.

  5. Mike Parker
    June 5, 2009 at 3:55 pm

    Ravishing Ruby (Tom T. Hall) is one of my favorites, as is Old Home Filler Up and Keep On A Truckin’ Cafe (CW McCall)

  6. J.R. Journey
    June 5, 2009 at 3:56 pm

    I remember the John Berry song. It was one of his better releases now that I listen again …

    Another favorite, though not an inspired choice, would be Alan Jackson’s ‘I Don’t Even Know Your Name’.

  7. Paula_W
    June 5, 2009 at 4:01 pm

    Though the song is not specifically about waitressing, Clay Walker’s “Chain of Love” has a waitress as a main character.

  8. Sam G.
    June 5, 2009 at 4:29 pm

    Five Chinese Brothers’ “She’s a Waitress (and I’m in Love)” was the first thing that popped into my head. A classic from the infancy days of alt-country.

  9. Mike Parker
    June 5, 2009 at 4:42 pm

    also Bruce Robison’s “Traveling Soldier” and Hayes Carll’s “Girl Downtown” are both, to some degree, about waitresses.

  10. Rick
    June 5, 2009 at 4:47 pm

    Tex Williams recorded a unique song about a truck stop waitress that resorts to murder to stop an annoying repeat customer who always ordered “Ham and Eggs”. I guess it was an early attempt to combine a murder ballad with a truck driver song! Yikes!

  11. Nicolas
    June 5, 2009 at 4:58 pm

    @Mike: So “Travelin Soldier” by the Dixie Chicks is a cover version? I didn’t know that

  12. Ben Milam
    June 5, 2009 at 4:58 pm

    throwing rocks at the moon by the backsliders

  13. Mike Parker
    June 5, 2009 at 5:02 pm

    yes, it’s a cover- Actually the first time I ever heard the song was when it was covered by Ty England.

  14. idlewildsouth
    June 5, 2009 at 5:06 pm

    Wow Mike. I didnt realize hed cut that. Listened to it on Amazon…he kinda sounds like Rodney Crowell on that cut.

  15. Lee
    June 5, 2009 at 5:09 pm

    “Eat At Joe’s” written by Matraca Berg and Gary Harrison and sung by Suzy Bogguss on her “Voices In The Wind” CD is one of my favorites.

    “Truck drivers, musicians with no place to go
    I can be your domestic goddess
    For an hour or so”

  16. Erik
    June 5, 2009 at 5:29 pm

    Reba’s “Somebody” is rather good.

  17. Dustin D.
    June 5, 2009 at 8:49 pm

    It’s a newer song but Jason Aldean’s “Wide Open” could rack up there also.

  18. Lazeras
    June 5, 2009 at 8:52 pm

    Always liked that “Chain of Love” song. Another favorite waitress song tho I don’t believe the girl is called a waitress in song, is Garth Brooks ” Everytime that it Rains”

  19. Chris D.
    June 5, 2009 at 9:34 pm

    I agree with “Somebody” and :Chain Of Love”, those are great songs.

  20. Buddynoel
    June 6, 2009 at 12:05 am

    Maggie’s Dream by Don Williams.
    “And they take her in their stories to places far away
    And leave her with the dishes, dreams and quarters.”

  21. Todd
    June 6, 2009 at 1:18 am

    Another one with a waitress as a main character is Joe Diffie’s “Bigger Than The Beatles”.

  22. Leeann Ward
    June 6, 2009 at 12:24 pm

    A great one is Kris Kristofferson’s “Here Comes That Rainbow Again”. Similar in moral payoff to “Chain of Love”, but less overtly sappy.

  23. Country Mike
    June 7, 2009 at 11:26 pm

    Brad Paisley’s “Two People Fell in Love” deserves honorable mention. Did y’all see that video?

  24. Gary Zarda
    June 8, 2009 at 9:03 am

    Kathy Mattea’s “She Came From Fort Worth” is awesome:

    She was workin’ at a diner just a week ago
    When a man from Colorado smiled and said hello
    And he turned her head with stories about a cabin in the trees
    Where the wind can sing you love songs beneath snow-capped mountain peaks

  25. Hard Times
    June 8, 2009 at 2:50 pm

    In “The Beer Drinkin’ Song” (circa 1980) by Lacy J. Dalton, she sings:

    Then there’s ol’ Dottie
    Down at the truck stop
    Been there since we were sixteen
    The only thing different, 20 years later
    Is the hip size on ol’Dottie’s jeans.

  26. Josh
    June 8, 2009 at 5:28 pm

    I’m in love with a waitress and I don’t even know her name.

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