I just pulled a heart earring out of the front tire on the Paramount, 
I was once on my way to an ice cream party and had a flat. I had to return the ice cream to the freezer and then fix flat. (It was ~100 outside). Retrieved ice cream, got to party and a carton was missing! Checked the next day at work and it wasn’t there…
I am still investigating The Case of the Missing Ice Cream
Frankie?
Had what I thought wasn’t a flat, but a slow leak. Examined tire and found a roofing nail straight through the middle of the tread. Removed nail and the tire instantly went flat.
My weirdest flat wasn’t all that weird, but gerund and I had just shown up to portland, eaten some pot brownies and were riding around. Suddenly we heard something that sounded like a gunshot, it was just my front tire but it freaked our stoned asses out.
Weirdest NON flat was riding home, i heard a clicking metal sound from my front wheel. I stopped to check it out and a staple shaped nail was stuck on my tire, unharming it. 
On my way to a Share the Road class to get my traffic fine reduced, I noticed a weird “DINK… DINK… DINK” noise coming with each pedal rotation and thought to myself “what the fuck… is my chain about to snap?” Got off my bike, chain was fine but a fucking screw had lodged itself through my tire, through my tube, and as I later found, right through my rim wall too (33h for the win). Needless to say I didn’t make it to the class.
Another time, my front tire’s bead rolled itself off the rim and started hitting the brake pad right after I hit a nice pothole… I thought I had broken a few spokes or something with all the noise and rubbing. Shortly thereafter, the inevitable explosion of the tube…
A nail head with about 1/4" of shank got stuck in a Vitoria CX tubular. I stopped with in a few rotations. Thought when I pulled it out I’d loose all the air but did’nt.
The tire is still good.
Also, not mine but a friends
[quote=DDYTDY]A nail head with about 1/4" of shank got stuck in a Vitoria CX tubular. I stopped with in a few rotations. Thought when I pulled it out I’d loose all the air but did’nt.
The tire is still good.
Also, not mine but a friends
[/quote]
holy shit, how did that happen?
when i had two sudden flat tires riding down my old hill on a really hot summer day after pumping up both my tires…
hope that never happens again
"holy shit, how did that happen? "
bead came off the rim while rolling. Strong tube…
one of the philly fixed dudes picked up a hypodermic needle with his tire once.
^^gnarly
Went to unlock my bike from the rack super late at night; started to roll away and the bike wouldn’t move. Looked back and someone had cut halfway though rear rim and a section of the rim had bent so that is slammed into the frame. Not really a flat but it was really weird. Thankfully I noticed before I tried riding.
i had a tube explode while the bike was sitting outside my friends house
last week i rolled up to a bike co-op to raid the free box and as i placed my bike on a locking rack the front tube’s schrader valve tore itself haflway off for some reason
also, i swapped from touring to knobbie tires on a touring bike. went from a good tube to four puncture flats while riding zero miles. i guess tire levers did it
?
I have had this happen while the bike was in my kitchen.
Got a normal flat, walked home, fixed it and set the tire down. It sat there overnight, then promptly blew off the rim as soon as I picked it up the next morning. Almost shit my pants.
Got the same nail in the tire thing as halbritt. As soon as the nail came out so did all the air.
Was riding drunk in the rain, decided to skid thru a puddle. There was an x-acto knife blade at the bottom of the puddle, never seen a tire go flat so quickly. Ruined a gatorskin too.
Had my bike hanging on my bike rack by the top tube, so the tires weren’t on anything. My roommate was sleeping and I was just on the computer when the tube just popped somehow that my roommate even woke up. To this day, I don’t know how that happened.
it looks like an anaconda is halfway through devouring the drivetrain
edit even though it is on the on the NDS. this is one badass anaconda
Not weird a all ,but scary.15mph off a turn into cobblestones during the Red Hook Crit in NYC… The explosion was epic. My front tire. Pop you hear in the video is not me though.
Woke up early one morning somewhere in nowhereville, CA the day I had planned to ride a century. Was staying at a B&B and breakfast was in an hour so I decided to go for a short ride to warm up the legs. Took off down the highway for a few miles and turned down a dirt road. Several miles down the dirt road I started getting worried about the state of things. I’d only brought one spare tube, no boot, and no patch kit for the century. I realized that if I got a flat, I would be in poor shape. I turned around headed back for the highway and as soon as I got going… KAPOW! A rock cut a nice gash in a brand new pasela tourgard. I booted the tire with a dollar bill, replaced the tube and rode back to the B&B gingerly. That dollar lasted through the entire century.