I've made a personalized mixtape every month for the last five years, combining au courant new hits, old favorites, random stuff overheard in convenience stores, Songs of Personal Emotional Relevance (the one from August 2008 mostly involves my wedding, which explains, for example, "Billie Jean"), ambient stuff that relaxes me in airports (very popular genre), etc. etc. As an example, I thought I'd share the January 2008 volume, which I think hangs together pretty well, considering.
Very brief notes: So we've got hot new indie-rock stuff (Vampire Weekend, the Juno-ascendant Kimya Dawson), recent events I was woefully late on (Franz Ferdinand's LCD Soundsystem cover, plus J. Holiday's luxurious " Bed," a/k/a the greatest song of all time), a track from the There Will Be Blood soundtrack done by a dude from Radiohead, actual Radiohead (was still absorbing In Rainbows, you see), reliable favorites ("Love Is the Drug," Electric Six), a highlight from the crazy Mars Volta concert I went to (they played for, like, eight hours), Marvin Gaye complaining about attorney fees, Youssou N'Dour singing sweetly, Lez (well, Led, but this'll do) Zeppelin wailing uncouthly, and Rahsaan Roland Kirk wailing even more uncouthly. Plus Alicia Keys' " Like You'll Never See Me Again," because she played it on Dick Clark's Rockin' New Year's Eve or whatever right after the ball dropped, and I dug it a lot. If you only have time for one song here, though, by god make it Swamp Dogg's version of John Prine's "Sam Stone," which is incredible, and plus his name is Swamp Dogg. Nothing here was airport-affiliated, oddly enough. But don't hold that against them.