my shirt is 15 years old:
SMART MEN GET LESS HAIR
(but they get more head)
Oh god, I love that. I HATED Twilight. Hate, hate, HATE it.
Probably my one Penguins shirt. It’s long-sleeved and fitted and it just says “PENGUINS” in copper rhinestones, like a Broadway marque. It doesn’t look like one of those glittery nightmares, just very simple. And then the Pens logo is underneath.
I really want this one baby tee I saw that said “Got Malkin?” with #71 under it.
Other than that, I’m not really a “tee-shirt” person. I like fitted, pull-over tops more.
I have one that says “I (picture of two hearts) Doctor Who.” I got it at a Dr. Who convention when I was in high school.
(For those of you who don’t know, the main character is an alien with two hearts.)
WANT! But can I get that with Nine or Ten instead of Eleven? 
Also want the ‘Doctor Is In’ shirt with Ten, complete with sonic screwdriver. Priceless.
My favoite is a gray tee with a picture of an Airstream Trailer on it and a caption underneath that reads “There’s No Place Like Home.”
I once saw a very tall fellow with a shirt that said (on the back) “Answer on front”, the front said “6 feet eleven inches”.
My current favorite is from Tee Fury and is a BSG/Battleship mashup … oh, look, I found it.
I have more Columbus Cottonmouths (minor league hockey) shirts than I will willingly admit to, but my favorite t-shirt has one of the Grateful Dead Bears in a faceoff with a skeleton and the caption “Steal Your Faceoff”.
My favorite is in oversized all-white with a picture of guy holding a can on ‘Whoop-Ass’ and the caption ‘Don’t make me open this!’
I’m wearing it right now. Long story.
This one was a page heading in the latest Bathroom Reader.
My security software said “Reported attack page!” when I clicked that link.
My fave tee shirt came from Rasputin’s Rock 'n Roll Store in Berkeley about 1980. It’s black with little white things which from a distance are reminiscent of sperm cells, but on closer inspection are seen to be little guitars with wavy necks. They are all headed toward the vinyl record on the upper left front. It gets worn mostly on Halloween.
I got my favorite in college.
I don’t really wear t-shirts anymore because in the San Francisco area it never really gets warm enough to wear one, but I used to have a fave that was a 50’s-style clip art guy holding a martini that said “Also available in sober!” T-Shirt Hell :: Shirts :: ALSO AVAILABLE IN SOBER
In high school I had one with that famous picture of Elvis and Nixon shaking hands that said “CULTURE” in big letters that always got a chuckle.
My current fave is a white hoody that says “You like this” in the Facebook font with a little “thumbs up” thumb next to it.
I have a red one with a stick figure in white that looks like it is burning with the letters DIAF beneath the figure. I love that shirt.
I lost my favorite t-shirt in a piece of waylaid luggage. It was from the movie Crumb. The front was a self-portrait of Robert Crumb (drawn in profile with a land holding a gun to his head) and a quote on the back from his brother Charles - “How perfectly Goddamn delightful it all is, to be sure.”
Other favorites are one for the Paul Green School of Rock Music, the Mad Scientists Union (Local #3.14…) and one for The Reverend Peyton’s Big Damn Band.
I have a grey shirt that says “Make Levees, Not War” that I got at a cheesy Bourbon Street tourist store when I was there after Katrina doing some volunteer work.
They had a really nice design with a big white flour-de-lis on black, surrounded by “I drove my Chevy to the levee but the levee was gone.” Unfortunately, the store only had a XXXL at the time, which would have comfortably fit two of me.
What? No one is wearing The Straight Dope shirt? I thought I was the only one who ever ordered one. 
My most recent one is from Punkin Chunkin
My all-time favorite was made/airbrushed for me by a friend back in college. The back had Maxwell’s four equations and the front said “Little Demon”
My current is from Hale’s Harley shop over in Ohio. Their shop is across from the local prison and the back shows a view of the shop through a set of bars and says “Room with a view”. The front has the standard Harley shield and says “Ride it like you stole it”. I bought extras and stashed them aside for when it wears out.
A few years back I went to PAX East, and got a black t-shirt with “Red Dead Redemption” written on the front in red letters. Apparently you couldn’t get the shirt anywhere else, as I’m constantly being asked where I got it.