“If you cannot teach me to fly, teach me to sing,” Peter Pan says in the enduring J.M Barrie classic, and ever since Wilbur and Oliver Wright invented and flew the first airplane, singers and songwriters have been taking that to heart and looking up to the skies for inspiration.

Country singers are no exception. Everyone from John Denver to Drive-By Truckers has got a song about flying of some description, and when it comes to airports and airplanes everyone has a different approach.

While Dierks Bentley is jetting off to Cancun and getting drunk on his Boeing 737, Cassadee Pope is still back at the airport lurking about and mooning over everyone kissing each other.

Of course, there has been tragedy too, and country music has lost some of its greatest voices to plane crashes over the years. Patsy Cline, John Denver and Jim Reeves are just a few of the country legends that have been taken from us too soon.

It’s like Miranda Lambert once sang: “If you don’t jump, you’ll never know if you can fly.” So, what are you waiting for? Take a leap into the unknown with our playlist of the Best Country Songs About Flying. Yes, ‘Free Bird’ is on it.

Listen to our Holler playlist of the Best Country Songs About Flying above:

1. 1.

   Drunk On A Plane

   Dierks Bentley

2. 2.

   Leaving On A Jet Plane

   John Denver

3. 3.

   Let Him Fly

   The Chicks

4. 4.

   Flying or Crying

   Zach Bryan

5. 5.

   Kisses at Aiports

   Cassadee Pope

6. 6.

   Time For Me To Fly

   Dolly Parton

7. 7.

   Fly

   Maddie and Tae

8. 8.

   Flyin' Shoes

   Townes Van Zandt

9. 9.

   The Cape

   Guy Clark

10. 10.

    Wings

    Jackson Dean

11. 11.

    Flying Visit

    Ferris & Sylvester

12. 12.

    Fly Over States

    Jason Aldean

13. 13.

    If Love Was A Plane

    Brad Paisley

14. 14.

    Free Bird

    Lynyrd Skynyrd

15. 15.

    Born To Fly

    Sara Evans

16. 16.

    Silver Wings

    Merle Haggard

17. 17.

    If You're Gonna Fly Away

    Faith Hill

18. 18.

    Outbound Plane

    Nanci Griffith

19. 19.

    Baggage Claim

    Miranda Lambert

20. 20.

    L.A. International Aiport

    Susan Raye

21. 21.

    Flying over Water

    Jason Isbell

22. 22.

    Eagle When She Flies

    Dolly Parton

23. 23.

    Expecting To Fly

    Buffalo Springfield

24. 24.

    Watching Airplanes

    Gary Allan

25. 25.

    All the Time in Airports

    The Handsome Family

26. 26.

    Boeing Boeing 707

    Roger Miller

27. 27.

    Let Her Fly

    Dolly Parton, Loretta Lynn and Tammy Wynette

28. 28.

    To The Aiport

    Nickel Creek

29. 29.

    I'll Fly Away

    Johnny Cash

30. 30.

    Fly Me to the Moon

    Willie Nelson

31. 31.

    If I Could Only Fly

    Merle Haggard and Willie Nelson

32. 32.

    Up and Flying

    Reba McEntire

33. 33.

    Faster than My Angels Can Fly

    Eric Church

34. 34.

    God Made Airplanes

    Jason Aldean

35. 35.

    Fly Trouble

    Hank Williams

36. 36.

    Outbound Plane

    Suzy Boggus

37. 37.

    747

    Lady A

38. 38.

    Airplane

    Indigo Girls

39. 39.

    Paper Airplane

    Alison Krauss and Union Station

40. 40.

    Shut Up and Get on the Plane

    Drive-By Truckers

41. 41.

    To Live is to Fly

    Steve Earle

42. 42.

    Tired of Flying

    Ryan Kinder, Brandy Clark and Jerry Douglas

43. 43.

    Flying Out Of London

    The Long Ryders

44. 44.

    Falling and Flying

    Hunter Hayes

45. 45.

    Flying Colors

    Keith Whitley

46. 46.

    Flying Cowboys

    Rickie Lee Jones

47. 47.

    Flying Silver Eagle

    Jamey Johnson

48. 48.

    Wings

    Kezia Gill

49. 49.

    This Plane Don't Go There

    Jason Aldean

50. 50.

    If My Heart Had Wings

    Faith Hill

Subscribe and Listen to Holler's Best Country Songs About Flying Playlist Above.

Dierks Bentley

Artist