Let's face it, we're at a point here where a lot of people are "introduced" to jazz later in their life. I was one of them. Most of the stuff that "inducted" me was jazz-funk or fusion and whatnot, but anyways, here's a look at what got me into jazz.
And make sure you come up with your own list in the comments, I'd love to post a second round with all your thoughts.
1. Chameleon- Herbie Hancock

I first heard this song in a medley of stuff that Maynard Ferguson and his band did when he dropped by my township's high school for a master class and performance. The persistent groove really stuck with me and I loved getting my non-jazz friends hooked on that bass groove.
2. Birdland- Weather Report

My bassist friend told me to give Weather Report a listen, so I went straight for Heavy Weather. It was a good choice. I still listen to that whole album, they're all genious. I now own this one on vinyl.
3. Kind of Blue (album)- Miles Davis

This one I heard much earlier then anything else listed here. I heard this album going into 4th grade and loved So What, Freddie the Freeloader, and All Blues.
4. Embraceable You/I Got It Bad And That Ain't Good- Louis Prima and Keely Smith

I never knew anybody was ever allowed to have this much fun, especially when playing music.
5. Salt Peanuts- Dizzy Gillespie

I dare you to listen and NOT say "Salt Peanuts! Salt Peanuts!" I mean, seriously...
Ok, well there's my list of 5 Songs that got me into jazz. Of course I left some out like Soul Bossa Nova, and anything Vince Guaraldi, but we'll save that for another time....
-jazzfreak11