Sorry if this is a bit long. I promise it isn't boring.
Any of your work that you'd like wiped off the face of existence because it now embarrasses you?
During my senior year in high school (2003/2004) I joined a band called Das Koon (short for Dashboard Koonfessional). They were originally a three-piece of guitar, bass and drums and before I joined they only had one song that only had one note and they would do shows where they played this one-note song over and over again at different speeds (each time introducing it as a new song, the slowest version being "the ballad") until the people organizing the shows would tell them to stop playing or cut the power.
A few months into their existence I joined as a keyboardist and for a short period we very productive. Although I had played keyboards before and had played guitar since I was maybe 8 years old, I was not a keyboardist nor did I even own a keyboard. I played a $17 toy keyboard that the guitarist got for Christmas. While I sometimes had a lot of fun with this band and we made some really cool music said music was not without it's issues. Some of my keyboard parts weren't even in key and many of the songs only had 2 or 3 parts a piece. That being said, the guitar, bass and keyboards almost NEVER did the same thing at the same time. There was a lot of call and response and rhythms that were bouncing off of each other. Sometimes the instruments would be grouped in pairs with the guitar and bass going together while the keys and drums were doing their own thing, all working together in a very strange and complex manner.
Our lyrics and song titles were probably the worst aspect. We had one song that I titled "Cigarettes In the Ashtray (Haha, Butts In Your Face)". When they weren't absolute nonsense they were usually intentionally and horribly offensive. There was a song that was originally titled "Dr. Martin Luther Koon Jr." with the only lyrics being:
"Hang him up
Watch him swing
Once was a king
Now watch him swing
We later shortened the title of it to "Dr. Koon" and the previously mentioned song to just "Cigarettes". We became a little more self-conscious after becoming aware of how cool our music actually was (which effectively ruined the band). While going through some of our old rehearsal tapes I found one song whose title I have since forgetten but it was played in a sing-a-long fashion (almost ballad like) with the lyrics:
"Love you more than a whore loves money
gonna give it to ya
gonna make you walk funny
We were a couple of Shakespeares.
We released two albums, the second mostly being a re-recording of the first in better quality with some of the songs left off, a few new songs added and a solo track from each member. The first CD was recorded in my bedroom over the course of a weekend using one microphone and minimal overdubs. It was very rushed (tracked in two days and I was given about 20 minutes to mix and "master" the whole thing) and I was very dissatisfied with the end results. The second CD was much more polished. We did the rhythm track in my parent's garage with about 8 mics, we each recorded some of our individual parts in the comfort of our owns homes on our own time and this time around I let the guitarist take care of the post-production stuff (I just didn't care anymore).
While Das Koon def had it's good points, sometimes I wish that those recordings didn't exist. I was recently going through many of my old band tapes, transferring them from my 4-track to my laptop and upon reading your post my first band immediately came to mind. To a degree, our music was absolutely brilliant but because of how bad other aspects were I could only describe the music as "brilliantly stupid". Some comparisons I heard were Talking Heads and The Velvet Underground.
Although we were pretty shit in some ways, I do recall that most of the shows we had were tremendous successes. People were absolutely blown away by what we were doing, usually saying things like "I've never heard anything like this". It was especially cool when we once attended a show a few counties over (just as audience members) and upon chit-chatting with some of the locals and revealing that we were from Ohio County one of the people asked "Oh. Do you guys know Das Koon?".