Doesn't have to be music you actually like, but all mine are actually in my iTunes library. I think it's a little more fun that way. Anyway lets see 'em.
I'll start with the cover of the Cake B-side collection, which is just awesome.
And of course Cake's Fashion Nugget can't not be mentioned, for songs like "Stickshifts and Safety Belts," "Race Car Ya Ya's," and most importantly "The Distance." I mean just look and listen to this awesome Speed Racer fan music video:
The Stroke's single Juicebox has a fantastic cover, and is a fantastic song as well.
Action Bronson's Saab Stories gets a mention for a great pun. He's also a total Jalop, rapping about cars that aren't just the basic status symbols, and bragging about Volks instead of Dubs. He also has a tattoo of an E36 Touring on his arm. Yes you read that right.
The Black Keys album El Camino has an extremely jalop cover, and a great story. It's the same van as the one they got their start touring in, a van with patina and fake wood paneling. The title is not just about being on the road (el camino means the road in Spanish), but a joke about the van being the muscle ute of the same name. What more do you want.
In a a very similar style to (perhaps even inspired by) El Camino, Kendrick Lamar's Good Kid, M.A.A.D City. A total tour de force, the album paints a vivid picture of his life growing up in Compton and is one of my favorite album's of all time. The cover depicts his mother's
Grand Caravan Town and Country, which plays a central roll in the album, as it provides transportation as he navigates the mad city that is his life. If there's anything on this list you should actually go listen to, it's this. Even if you aren't into hip hop, I promise you'll find something worth your while.
Finally, I'll add a couple mix tapes by RnB singer and Odd Future member Frank Ocean. Both feature his own cars; an E30 M3 and a Foxbody Mustang. Yup.
So that's a sampling of my list. What about you? I'm sure you'll have some stuff I haven't heard of, which is fantastic. I always like expanding my horizons.