Friday Five: Songs About Waitresses

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.

• 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.
• 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.
• 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.
• 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.
• 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