Blue Train
If potential convert is a technophile, possibly Ben Allison & Medicine Wheel's Riding the Nuclear Tiger.

I'd go with Rollins - "Saxophone Colossus"; it starts off with the funky and accessible "St. Thomas", has a great ballad, the recognizable "Die Moritat", and the innovative "Blue 7". In my view the perfect intro to jazz, and the first jazz album that I loved.

Another good one is Bill Evans; "Waltz for Debbie", I've had many non-jazz fans comment on how much they liked it when I've had it playing at get togethers.

I think the spareness of the non-piano trio makes it a little less accessible, still a great album though. "Now's the Time" is another good Rollins intro.

Yes! I would highly highly highly suggest The Complete Quartets with Sonny Clark. One of my favorites of all time. If you're a jazz-guitar fan, you'll love this.

Depending on your experience, jumping into Sun Ra, Dolphy, or some of Coltrane's later work can be intimidating and a lot to take in with nubie ears.

I loves Jimmy Smith - teriffic B3 player, funky, soulful and great to start off with. He's got an amazing duo record with Wes Montgomery, but just about anything of his will knock your socks off. Not your standard sax quartet, and I think a pop guy would respond to his badass keys.

Wayne Shorter is also great. Tasty sax player, but maybe a little more concise than a Coltrane. Juju and Speak No Evil are killer.

This is how I really got into the genre as well - & Yail beat me to the suggestion. In addition to stations you can find on the Web, I'd also recommend trying the "jazz" channel on yer cable/satellite TV, if you have a package that comes with XM or Music Choice.