Random Rules Playlist 026: The 105 best songs about Florida, ranked

Apparently I'm not the only one to have a complicated relationship with my home state

Even though I was born in Kentucky, I spent more time living in Florida than anywhere else in my life (off and on for about 24 years). My parents moved us to Miami when I was about three months old. We moved around a lot because my father was a minister (that’s a whole other topic which maybe I’ll get into later). I ended up living all over the state: Orlando, Jacksonville, Tallahassee and small towns in between. My most formative years (high school) were spent in Jacksonville, and the city I visited most often but never lived in was Gainesville, because of high school friends who ended up there and because of the music scene there (I procured my first fake ID in hopes of attending an Afghan Whigs / Spinanes show at the Covered Dish in Gainesville - don't worry, it worked like a charm). My parents lived in a few other parts of the state after I moved away; Eustis, Crystal River and Largo (near Tampa) so I got to know those places a little through visits at the holidays.

I have a few Florida institutions to thank for helping me discover good and more obscure music - namely WVFS in Tallahassee, a station I listened to on trips to visit my grandparents throughout my childhood. I used to buy a brick of blank tapes before we left to visit Tallahassee and I’d tape as many hours of WVFS programming as I could (with the volume turned down) and then try to make sense of the recordings when I got back home. I eventually ended up working at WVFS when I was at FSU in the late 90s. The other FL institution that shaped me was Einstein A Go-Go in Jacksonville Beach, an all ages live music venue and dance club that also had a record store attached with clerks who were eager to offer up recommendations. Growing up in Florida wasn’t the worst thing ever, but I was definitely ready to get the hell out of the state when the opportunity presented itself to me around 2001 (obviously years before wannabe Hitler, AKA DeSantis wrecked the place and steered it towards the fascist state it’s become more recently).

If you listen to all 105 songs on this playlist (6 and a half hours) you’ll start to notice some themes that summarize the ups and very extreme downs of being in Florida, whether it’s a lifelong stint, during Spring Break or a wild, Zola-style road trip. There’s a prevailing sense of desperation in a lot of these songs (but definitely not ALL! Freddy Cannon does seem to be very enamored with the state!)

The theme of being lost or in a bewildered state seems to pop up a lot, on tracks by everyone from Frank Ocean to Tom T. Hall, to Taylor Swift feat. Florence + The Machine. Drugs, especially cocaine, get more than a couple shout outs, along with sunburns, hurricanes and sexual deviancy. Some of my favorite songs here are the handful of tracks about the Everglades, especially Waylon Jennings’ ode to the massive swamp land with references to two of the state’s biggest villains; mosquitoes and gators. There’s also the outright anti-Florida takes, like Against Me!’s “Sink, Florida, Sink,” Graham Parker’s “I’ll Never Play Jacksonville Again” (as someone who has been to a lot of shows in Jax……like, OK, fair!) or the Melvins’ “Stop Moving To Florida.”

I should note that the songs that initially inspired me to make this playlist were Palace Music’s “Gulf Shores” and “West Palm Beach” (check the time stamp on these on the playlist) which were originally released as a 7” single in March of 1995. I would be lying if I said that the release of “Florida!!!” from Taylor + Florence didn’t motivate me to finish this playlist a bit sooner than planned, but I really didn’t know until I started doing my research just how many songs there are about Florida (or that at least mention Florida, or a city in Florida in the lyrics). Please don’t ask me to do 49 more of these state-themed playlists! Without further ado, here’s the list:

RANDOM RULES PLAYLIST 026: THE 105 BEST SONGS ABOUT FLORIDA, RANKED

1. “Orange Blossom Special” - Johnny Cash

2. “FloriDada” - Animal Collective

3. “See America Right” - The Mountain Goats

4. “Florida Boy” - Rick Ross, T-Pain & Kodak Black

5. “Going Back To Florida” - Bumble Bee Slim

6. “St. Pete” - Shannon Wright

7. “Florida” - Wild Pink

8. “The Everglades” - Waylon Jennings

9. “Tallahassee Love” -T-Pain

10. “Florida Bound Blues” - Bessie Smith

11. “West Palm Beach” - Palace Music

12. “Deep Down In Florida” - Muddy Waters

13. “St. Augustine” - Band of Horses

14. “Orlando” - Miriam Makeba

15. “Tallahassee Lassie” - Freddy Cannon

16. “Sink, Florida, Sink” - Against Me!

17. “Gulf Shores” - Palace Music

18. “Florida!!!” - Taylor Swift feat. Florence + The Machine

19. “Bitch, I’m From Dade County” - Evil Empire, DJ Drama, Trick Daddy, Trina & Ross

20. “Lost In Florida” - Tom T. Hall

21. “Pensacola” - Deerhunter

22. “Lost” - Frank Ocean

23. “Florida” - Luke Temple

24. “Florida’s On Fire” - Superchunk

25. “pensacola” - Oso Oso

26. “South Of The South” - David Dondero

27. “Prison on Route 41” - Iron & Wine / Calexico

28. “Florida State” - Jody HiGHROLLER

29. “Gainesville” - Tom Petty

30. “Orlando, FL” - Into It. Over It.

31. “Tampa” - Small Black

32. “Dade County Cops Don’t Quit” - Air Miami

33. “Everglades” - Dale Hawkins

34. “First Few Desperate Hours” - The Mountain Goats

35. “Gainesville, Fla” - John Vanderslice

36. “Everglade” - Anohni and the Johnsons

37. “Florida Kilos” - Lana Del Rey

38. “Florida” - The Range

39. “florida” - mxmtoon

40. “Everglades” - Sea Urchins

41. “Butchered Tongue” - Hozier

42. “Bad Seed” - Glen Campbell

43. “Florida” - Modest Mouse

44. “Florida” - Lonnie Mack

45. “Florida” - Push Kings

46. “Orlando” - Trans Am

47. “Orlando” - Exploded View

48. “Florida” - Vic Chesnutt

49. “Tallahassee” - The Mountain Goats

50. “Daytona Beach” - Half Japanese

51. “Florida” - Princeton

52. “Florida (203)” - Sacred Harp Singers of Chatahochee Singing Convention

53. “In Florida” - Land of Talk

54. “Long Time Man” - Nick Cave and the Bad Seeds

55. “Daytona Sand” - Orville Peck

56. “In Florida” - Jake Xerxes Fussell

57. “The Bass That Ate Miami” - Maggotron Crushing Crew

58. “O Homem Da Gravata Florida” - Jorge Ben

59. “Working On The Highway” - Bruce Springsteen

60. “Florida Rain” - Matt Bauer

61. “Apalachicola” - Gillian Welch

62. “Jacksonville” - American Aquarium

63. “Florida” - Grandaddy

64. “Miami Memory” - Alex Cameron

65. “Pensacola, Florida” - Night Shop

66. “Fort Lauderdale” - The Impacts

67. “Gainesville” - Pure Bathing Culture

68. “Miami” - Cate Le Bon

69. “Florida Twist” - Bill Haley and his Comets

70. “Key West (Philosopher Pirate)” - Bob Dylan

71. “From Tallahassee to Gainesville” - Gold-Bears

72. “The Everglades (For Leonard)” - Blur

73. “Disney World” - Blind Mr. Jones

74. “Orlando” - Rick Bain and the Genius Position

75. “Rafting Starlit Everglades” - Baths

76. “Gainesville” - Dillinger Four

77. “Everyone In Jacksonville” - Emperor X

78. “G-Ville As Rare Factions” - The Cadets

79. “Florida Time” - Bob Seger

80. “Fountain of Youth” - Guided By Voices

81. “I’ll Never Play Jacksonville Again” - Graham Parker

82. “Clearwater” - They Hate Change

83. “Everglade” - Cannonball Adderly

84. “Florida Storm” - Southeast Alabama and Florida Union Sacred Harp Singing Convention

85. “Tallahassee Days” - Dead Prez

86. “Moon Over Miami” - Bill Haley and his Comets

87. “Florida” - Khen

88. “Miami” - Baxter Dury

89. “Oceanographer’s Choice” - The Mountain Goats

90. “Daytona 500” - Ghostface Killah, Raekwon, Cappadonna

91. “Snowbirds and Townies” - Further Seems Forever

92. “Blank Florida” - Hazel

93. “Coconut Grove” - The Lovin’ Spoonful

94. “Miami” - Randy Newman

95. “Moving To Florida” - Butthole Surfers

96. “Stop Moving To Florida” - Melvins

97. “Orlando” - Population II

98. “City of Ocala” - A Day To Remember

99. “Sarasota” - Balkans

100. “Florida” - Junior Varsity

101. “The State of Florida” - Less Than Jake

102. “Boca Raton” - Bas & A$AP Ferg

103. “Biscayne Block Boyz” - Otto Von Schirach

104. “St. Augustine at Night” - Dawes

105. “Polk County Blues” - Ella Mae Wilson & Richard Williams