I got a trio of T-shirts for Christmas from a fellow musician friend. The t-shirts each span a decade (approximately) and they contain silhouettes of popular musicians.

My friends and I have been having fun with the 1980's one. The company doesn't provide an answer key, they want folks like us to guess. They have a low-traffic flickr thread going, but my friends and I have a much more successful high traffic livejournal thread going.

Full color image of the T-shirt here

Numbered list version here, harder to see the white callouts

Each silhouette has been, so far, more than just an image of the artist in question. Each one has been somehow iconic: Either an album cover shot or a particularly iconic image from a very specific music video, and for almost all of our guesses, we've been able to back them up with Youtube clips or images found on the web, each one unmistakable. And of course, each artist is absolutely definitively "80's" by some definition, so it would be a waste of time to guess, for example, "Elvis" unless you mean Costello.

Here's what we've got so far:

1 David Byrne, specifically from the Stop Making Sense tour.
2 Boy George
3 Joe Jackson?
4 Madonna
5 Michael Jackson
6 (*NOT* Flock of Seagulls: Synthesizer type is wrong. Can't find an example image of Howard Jones with that type of keytar, the one in the "New Song" video is a different type.)
7
8 Cyndi Lauper
9
10 Tina Turner
11 (Lots of guesses on this one, can't nail it down exactly.)
12
13 Annie Lennox, specifically from the Sweet Dreams video.
14 Bono, specifically from Under A Blood Red Sky.
15 David Lee Roth
16 Glenn Danzig (the Misfits)
17 Eddie Van Halen, specifically from the You Really Got Me video, where he played an Ibanez explorer knock-off instead of one of his more famous frankenstrats. Still not entirely certain about that one?
18 (guitar is not big enough to be Brian Setzer, otherwise that would be our guess.)
19 (hair would suggest Kate Pierson of the B-52's, but I can't find an image of her with that collar and belt. Perhaps Sheena Easton from the "Swear" video? Can't tell for sure)
20 (Unclear. Maybe Mark Knopfler from the Money for Nothing video? But the headband isn't called out in white, and I'd expect that if it were so.)
21 (Robert Smith of The Cure? Can't find an image of him in that pose, though.)
22 John Cougar Mellencamp
23 Sting, specifically from the Every Breath You Take video.
24 The Dead Kennedys, "Pull My Strings".
25 Prince
26
27 Billy Idol
28
29 Danny Elfman, "Dead Man's Party" era.
30
31 (30+31 are a duo, so random guess of Hall and Oates?)

Videos, from top left:
d/k (near #3) (Vixy argues Max Headroom, but I say too pointy for that.)
ZZ Top, "Legs" (near #5)
d/k (near #7)
d/k (other near #7)
A-ha, "Take On Me" (top right corner)
Irene Cara, "Flashdance" (near #2)
d/k (near #6)
"99 Luftballoons" (near #9)
d/k (near #13)
The Clash, "Rock the Casbah" (near #17)
MC Hammer, "Can't Touch This" (near #22)
d/k (near #23)
MTV station ID (near #25)
d/k (near #27)
d/k (near #29)
d/k (near #31)