Here's an article about the lost art of actually making a mix tape on a cassette, which was the way I did things -- old school. It's worth a read.
Compiling a mix tape is also, of course, a labour of love, an act of dogged devotion. You can see why Nick Hornby used the mix tape in High Fidelity as a signifier of love and devotion. If my memory serves, his male protagonist, a romantic loser, wins his long-suffering girlfriend back by compiling her a tape of songs by romantic losers about romantic losers. On some Freudian level, the compilation tape says more about the compiler than the object of his or her devotion.
'It takes time and effort to put a mix tape together,' writes Dean Wareham, leader of the short-lived, but quietly influential, art-rock group, Galaxie 500, in a book called Mix Tape: The Art of Cassette Culture, which was edited by Thurston Moore of Sonic Youth. 'The time spent implies an emotional connection with the recipient. It might be a desire to go to bed, or to share ideas. The message of the tape might be: "I love you. I think about you all the time, listen to how I feel about you." Or maybe: "I love me. I am a tasteful person who listens to tasty things. This tape tells you all about me." There is something narcissistic about making someone a tape, and the act of giving the tape put the recipient in our debt somehow. Like all gifts, the mix tape comes with strings attached.'
A mix tape is, for lack of a better way to put it, the best gettin' to know you chit-chat you could ever come up with.
However, if you believe that the best live show you ever saw was Justin Timberlake, keep your f@#!in' music to yourself. The mix tape has to have obscure, unheard of greatness to it, and "Sexyback" will never, ever make the cut. Ever. It will make the recipient of the mix tape say "This is teh Suck," and, by extension, that you suck and aren't worth any more time. As you can tell, it is important to execute on your strategy by using your wits and cunning, and leaving that shitty pop music behind. Sound off like you've got a pair!
Seems to me the key to making a proper mix tape (even if you're cheating with iTunes and burning CDs like I will be) is putting songs on there that you don't hear all that much. If you are making it for someone else, then find a whole bunch of songs you think the other person has never heard, and perhaps will find unlistenable, but that you love. Primus' "Tommy the Cat" being a prime example for me.
Anyhow, I will update this post after I compile the playlist, and we'll see where we get. I already know song # 1 is "Summer Babe" by Pavement. Please discuss in the comments, all 2 of my readers.
UPDATE: So here it is:
1. Summer Babe -- Pavement
2. Shut up and Get on the Plane--Drive by Truckers
3. Sweet little Thing--Lucero
4. We're not Alone--Dinosaur Jr.
6. Two Doors Down--Dwight Yoakam (acoustic)
7. I Want you So Hard--Eagles of Death Metal
8. Give you my Car--Flys
9. The Ballad of the Gravel Pit--Gravel Pit
11. Sunday Morning Comin' Down--Johnny Cash
12. Paper Thin Walls--Modest Mouse
13. Tommy the Cat--Primus
14. I'll Just Fall--Lucero
15. Sugar Kane--Sonic Youth
16. C'mon C'mon--Von Bondies
17. Goddamn Lonely Love--Drive by Truckers