Mixtapes, or Mix CDs, are awesome. I love getting them. But I mostly like making them. To me, it's an art. Taking songs you like and trying to find a right mix to appeal to someones differing taste. Or, sometimes, taking music of a similar taste and blending in new music with it. Or, sometimes, doing mood mixes or, another one I like, self-made soundtracks.
The best way to make a mix is to know who you're doing it for and what kind of music they like. If they don't like death metal then you need to know your limit(which would be right about Slayer). If they're strictly oldies you might need to track down some classic oldies by 1 hit wonders. The kinds of songs you remember but never knew the musician. Plus maybe throwing in some of the classics. Really depends who you're making it for and their interests. After that, time to set up your track listing. In my opinion, you need 2-3 good opening tracks that really play to their interest. If they're really into metal then blast out something really hard. Maybe something they might know with something similar. 2-3 in the middle to make sure that they don't just keep flipping through. Something they may know or similar. I'm all about throwing a classic on a mixtape someone might not have heard in a while. Kind of like the song in the background of a movie they may like, a cover/hard to find track by a fav band of their they may not have heard, or something similar. Then again, nothing wrong with a classic radio hit out of nowhere like some more Human then Human or old school Tupac. Plus a big number to go out on. What I mean by that is, and I like doing this, is to throw a song someone may not know but comes off as epic or emotional. Or even something they know, but the kind of song you can close an album on. Like, I don't know, if I'm doing an industrial mix I throw on maybe a slow Ministry track like So What or Filth Pig. Doing something more mainstream maybe some of KoRn's more heavy but slow songs. Then again, sometimes you just need to kick ass on an end song and hit him with something hard or upbeat. Depends but I like to maintain a flow. I hate switching from one style to a completely different one or one fast bpm to a slower paced song. Unless that's the point. Also, compilations, soundtracks, and best of's are always a help making mixtapes. you can always find a treasure buried there. Plus the net. Go to Amazon if you have an account and look under music recommendations, check CDuniverse's acts like that, including "People Who Enjoyed This Bought..." and other sites and then download some sample tracks. I've discovered some of my new a favorite Ayria, Amy Winehouse, and Birthday Massacre.
I started making real mixtapes after I sort of settled into my tastes when I was in high school. More hard rock at the time but starting to get into industrial underground music. I didn't make too many just ones for my friends. usually with stuff they couldn't find that I had. I remember getting this really cool industrial/goth mix from a sexy goth girl in High School(who also turned me onto Johnen Vasquez comics) that helped expand my own tastes. I really started nailing them out after a few years when my collection starting building with bands like Thrill Kill Kult, ministry, Skinny Puppy, and other industrial/goth/hard rock underground acts. My best friend Jay Jay never dug my music until I started making a series of mixtapes. I knew he was in 80s new wave, alternative rock of the 90s and some hard rock/metal so I used that as a basis for my mixes. After a while, pssh, Jay Jay now listens to a majority of the music I listen to.
For work one year I made mix CDs for all my co-workers. Ranging from mixes of 80s and hard rock, to all rap, to even all oldies. Most of my co-workers loved them. I think all of them did. I got enough of a collection, or access to other collections and knowledge of genres, to make mixes of almost all types. okay, maybe not emo or, show tunes, orchestra or World.
Just recently I started making my buddy and myself a set of mixes. His comment about me being able to do my own radio show got me to making these ones I call Warp City Radio(after a Ministry track) of anime music, industrial-related, and whatever else I think fits. I gave him a bunch with no track listing and he told me it just goes all over the place like a radio station but all works.
I also like doing soundtracks. Usually to comics but I did two to Avatar: the Last Air Bender. Those are kind of hard because I try to find songs that match the shifts in mood and events. I'll post some later this week.