Where The Wind Comes Sweeping Down The Plains...
This is the most obvious place to start, love it or hate it. The original film was released in 1955 and is the one with which most people are somewhat familiar. This one is from 1999 and stars Hugh Jackman of Wolverine fame. I'll spare you other tracks from either film, but you know they're out there and fairly easy to get.
The Farmer and the Cowman
OK, I lied. I just couldn't help myself. The whole farmer/rancher conflict is just too legit to ignore, and this is the most irritating - i.e., memorable - way I've found to stick that in their little brains. This one's from the 1955 version - just in case you hadn't figured that out from watching.
Oklahoma (The Call) - From Reconciled (1986)
Michael Been, the primary creative force behind The Call, and drummer and occasional co-writer Scott Musick, were both from Oklahoma originally. The Call was a respected, if somewhat 'alternative' band in the 80's and 90's. This song incorporates some Oklahoma-specific imagery and emotions, although it's not a historical song by any stretch. It was one of the ten finalists for Oklahoma's Official State Rock Song when such a thing was voted on in 2009.
Do You Realize? (The Flaming Lips) - From Yoshimi Battles the Pink Robots (2002)
This track won the 2009 state-sponsored contest to become Oklahoma's Official State Rock Song in 2009. When it became time to renew that via "Executive Order" in 2013, Governor Mary Fallin simply could NOT find the time - probably because one of the band members wore a red hammer and sickle shirt when visiting the Capitol at some point after the song was chosen. Lead singer Wayne Coyne may also have used some rock'n'roller type potty language during an event at which the band was honored.
Why can't these rock people be more like country people - you know, REAL Americans?
All four members of The Flaming Lips are from the OKC area, and are one of Oklahoma's most bizarre and reputable non-country musical exports. They are more than a band - they are an experience.
Never Been to Spain (Hanson) - Live Version (2008)
This song was written by Hoyt Axton of Duncan, Oklahoma, and became a hit when recorded by Three Dog Night in 1971. It was recorded multiple times thereafter, including versions by Elvis Presley, Waylon Jennings, and Ike & Tina Turner. This version is from Hanson, Tulsa boys who - despite what you may have heard - are still very much alive and well and making pretty amazing original music on a regular basis.
Oklahoma (Bishop Allen) - Live Version (2009)
Oklahoma (Bishop Allen) - Album Version (2009)
I don't know that this track has much to offer in terms of history or culture, other than the name. Bishop Allen is from Brooklyn, so perhaps the name and internal references are more about impressions and emotions than anything. Catchy tune, though.
Thinking 'Bout Something (Hanson) - From Shout It Out! (2010)
Technically every Hanson song is an Oklahoma song, but this one's video takes place on Greenwood Avenue, packed with locals. The scene is a parody of a song in The Blues Brothers movie, and yes, that's Weird Al playing the tamborine. Also, I love this song.