I'm not sure what a true "Jeeping" song is...
I've got a couple of playlists on my Ipod that I built for Jeeping....mostly for specific trips. One for summer roadtrips into Montana, one for winter wheeling in the foothills, one for a day trip to Lethbridge....
For songs with lyrics that include offroading, I'd suggest "Truck Got Stuck" by Corb Lund if you don't mind a bit of intelligently written country music.
Also "Back Seat of My Jeep" by LL Cool J, if you're fan of older hip hop.
A quick Google search shows a song called "The Jeep Song" by the Dresden Dolls...but I've never heard of them before now and I don't have the bandwidth here to download anything.
Also from google, Rebekkah Dreskin has a song called "Jeep Boyz"...but again I've never heard it.
Ah...jackpot. Some thoughtful soul has already made a list :bounce:
I can't take credit for this, it was posted by someone called Gullywhumper on blog.allthingsjeep.com
Some Jeep songs found on iTunes:
Jeep Jockey Jump 3:08 Glenn Miller & The Army Air Force Band Army Air Force Band
Jeepster 4:08 Electrik Cokernut Best Of Moog: Electronic Pop Hits From The 60's And 70's
Buddy Leave My Little Jeep Alone 2:05 Raun Burnham
Jeeps Blues/Funky Jeep 8:20 Gottfried Böttger & Reiner Regel Reedin'
Jeep Bounces Back 5:36 The Mac Duncan Jazz Band Live At the Lord Napier 1973
Jeep Boogie 2:59 Cow Cow Davenport Cow Cow Davenport Vol. 2 (1929-1945)
The Jeep Is Jumpin' 4:51 Coleman Hawkins, Duke Ellington & John Coltrane Duke Ellington Meets Coleman Hawkins
Little Bo Beep Has Lost Her Jeep 2:04 Spike Jones (Not) Your Standard Spike Jones Collection Country
Ridin' In My Jeep 3:04 Justus Boyz Uh-Oh Dance
Jeeps Blues 4:10 Duke Ellington & His Orchestra Duke Ellington - Master Protection Jazz 13
Jeep Is Jumpin' 3:07 Faux Frenchmen Faux Frenchmen
Three Day Beard and a Rusty Jeep 2:40 Bill Emerson Bill Emerson and the Sweet Dixie Band Country
The Jeep Is Jumping 4:54 Earl Hines Earl Hines Plays Duke Ellington
I hope that helps. When I'm working on a playlist, I generally just arrange my music alphabetically by artist (all on Itunes so this is easy to do), and skim through it, picking out songs that match the mood or theme that I'm targeting. I throw them all into a playlist in the order I find them, and then once I've added them all I will fine-tune the order that they are played in. Generally this gets me to 90% of what I want, and I will fine tune it with additions/subtractions after one listen through it.