I started it, I have to go first.
My Datsun 1200's battery was dead so I thought, no problem, I'll bump-start going down this hill. Kept trying all the way down and it absolutely failed to start. It was only after I got all the way to the bottom (meaning it was uphill in both directions) did I realize I never switched on the ignition. Sigh...
Stuffed an ej20 twin turbo in the back of a very rusty fiat 850 spider. Driving the result was a combination of exileration and pure terror. It actively tried to kill you.
I didn't know I hit the mud puddle hard enough that the front axle of my CJ-3A kissed the oil pan and leaked started to leak oil. I also didn't know that when it's squealing like a stuck pig that I should have turned it off earlier. I will blame it on the fact that I was just 16 years old.
it was my first time customizing a car and learning to work on things.
so in my rusted out 1990 corolla I put 2 12" subs (from a home stereo) and powered it through an amplifier (from a home stereo) using a AC/DV inverted through the cigarette lighter.
good times...
it would literally shake rust off the car when the volume was turned up, but not for very long because the inverter would start beeping and cut power. We eventually remedied it to a proper stereo with a vented box for 2 12" subs with LEDs that took up the entirety of the trunk space and wired it through a traditional stereo headunit. Then it really shook the rust off.
I was also 16 years old...
Unfortunately, it's a pretty long list.....
I once asked my mother if she'd ever been airborne in her car----- before she could say anything I had taken the "jump" where they were laying new asphalt over the old road. The car got air....her head smashed the roof. I got grounded. Yes.....I was 16.
I also managed to disable my Dad's GTI by understeering into a curb. A day later the control arm bushings in my 66 Chevelle gave way after an off-road excursion. My Mother, disgusted, had me clean the garage thoroughly. I decided to park her Buick outside so I could sweep the garage floor. Then I forgot to close the driver's door as I pulled out of the garage. 
I ended up damaging her door so badly it wouldn't close AND I screwed up the garage door rail to boot! They still bring that one up!.......and yes.....this also happened when I was 16. (seeing a trend here?)
there's plenty more......but you just asked for one.
my first car was a 1990 Grand Marquis.
I don't know how I managed it, but one day during college, I got in it, started it up and immediately found myself doing a (studded snow tire in mid-summer) full-throttle burnout toward the garage door which was about 20 feet away.
Immediately slammed on the brakes, turned off the car, legs shaking, got out to walk around for a few minutes and regain my composure hoping none of the neighbors noticed. Nice track of rubber on the concrete driveway accented by score-marks from the studs xD
Still not sure what my brain-autopilot was thinking that day or what even happened.
To this day, every time I get into and start up a car that isn't manual, I have to stop and think for a second about my feet, where they are, make sure I'm in park.... so I don't accidentally do this again (because I don't own any automatic cars myself, and I always feel like I'm forgetting something when I start one up.... and crashing someone else's car into the garage would just be, well.... inconvenient).
Hmm, 16...
In high school auto shop, we learned to clean and re-grease wheel bearings. My buddy had brought in his mom's green/faux wood Ford station wagon and we took everything apart. While my buddy installed the new bearings, I - for fun - cleaned off the old ones. I found that holding the inner race and blowing it with compressed air, made a sound much like a turbine spinning up*. I thought, hey, cool, wonder how fast I can make it go. Later, back-calculating the math based upon the pitch of the sound, I can factually say that you should not drive a green/faux wood Ford station wagon faster than 2300 mph, or the ball bearings shoot out of the housing and fly all over the garage, with everyone ducking for cover.
*Yes, I am well aware that I was holding the first "fidget spinner" but wasn't smart enough to know it.
25mph roll, jam into reverse and dump clutch trying to impress the cheerleader. Did NOT end well.
I tried to drive a stickshift Volvo with just my right foot while my left foot was outside the open driver's door. Coincidentally I rammed it in to my toolbox in front of it.
Volvo was unscathed, tool box nearly folded in half.
My brother, when he was, hmm, 16 I think, had a Ford Galaxy that had an interesting feature and demonstrated it one day. He drove up a hill and floored it, whereupon the gas pedal magically pulled away from his foot and went straight to the floor. I asked how he dealt with that and he said he just turned the key off. Oh, okay, and neither of us thought anything more about it. The fact that it was a broken engine mount never occurred to us until years later. At the time though, it was just childlike wonder that we accepted what it did as apparently normal.
I'm not sure if it was the dumbest thing I did with a car, or that my parents did. I, as a 5-year-old, was sleeping peacefully in the back of the '65 T-bird when we got home. Dad was gonna be sanding the picnic table he just built, so they left me there. Well, I woke up, played with the shifter, and the car ended up drifting backwards through the garage door, almost pinning Dad to the picnic table.
I had a real nice 180° spin on a backroad one time, as a result of a good song being on the radio.
Ah, 16 seems like none of us had any common sense at that age. I was riding my dad's motorcycle (with permission) and had been out for about 5 miles or so and it sputtered to a stop. I tried all sorts of things to get it to refire but nothing would happen. The one smart thing it did was quit before i killed the battery. I finally walked to a nearby house and called him to come rescue me. First thing he checked was the fuel petcock, I had forgotten to turn it on. Too bad that wasn't the last time I did something dumb with a motor vehicle....
In reply to Joe Gearin:
I agree.... lots of dumb things. There was the splitting the Y-pipe on a 4.3 V6, running dual glasspacks and dual 3.5"x18" tips to a full size chevy. At speed you couldn't hear ANYTHING the resonance was so bad.
There was the full parking lot burnout in dad's 9C1..... it was white. that cost me $10 in quarters and a half hour at the car wash scrubbing rubber off the rear quarter.
There was the "90mph on a gravel road in a 1984 Ford Tempo because curfew is past" where the car got caught in some jack-wagon's ruts that threw it sideways.... at 90. I poo'd a little. and pee'd.
There was the moment I put 700lb front springs on coilovers on a daily..... that weighed 2700lbs. and tried to take the wife on a sunday drive an hour and a half each way.
At 16 I seriously didn't realize you weren't supposed to catch air in a car like the Dukes of Hazard, Smokey & the Bandit, etc. My parents never did understand why the wire for my fuel sending unit & air lines for the rear air shocks kept getting destroyed.
At 19 I drove down an abandoned railroad bed one night, then reversed when we found a bridge that was impassable. The rear wheel caught some loose gravel along the edge & pulled the car 1/2-way off until it was high-centered. That was a long walk back...
In reply to Pete Gossett:
That was the one thing I did know at 16. I had to put ball joints on that tempo just to start driving it.... so I knew how fragile they were. My GF's 69 Delta 88? That thing I swear spent more time airborne than on the road. 455 4 door lime green with all 4 springs sagging... it looked bagged.
Sold my ratty 1966 Mustang for $500 in 1973 after trashing right rear quarter panel against a tree. It was a 289. And a fastback. Of course then it was just an old wrecked car.
Oh yeah....did I mention it was a real Shelby GT350H? 
I bent all the valves on my dad's engine by putting a bolt in the wrong spot. I also essentially destroyed a whole engine with a piece of spark plug porcelain. I've broken my own pistons due to boost-related mishaps probably half a dozen times. I hooked jumper cables up backwards in the dark and started the car, which resulted in a very minor fire and some wiring repair. I've spun out in front of several very massive vehicles learning such things as 'bumpstops approach infinite spring rate'. Lowered my car so much i broke axles, oil pan, and trans pan. Left spark plugs out of an engine for a few months and then found out that one cylinder was full of pebbles due to mud dauber wasps AFTER i installed it and tried to crank it. Accidentally ran my car into a fence when i forgot to pump the brakes after a brake job. Accidentally let a customer drive off with a loose crank pulley bolt after i cranked the engine with a ratchet still on the crank. Left lug nuts loose. Drove on a loose axle nut and ruined a wheel bearing. Left pinch bolts out of ball joints on a car i dropped the engine from and had the ball joints pop out of the control arms when i pushed the car out of the bay. Broken engine block mount ears. Let block freeze with water in it. Shifted into 2nd gear at 80 mph. Cracked transmission cases. Accidentally driven one car i own into another car i own in a stupidly overcrowded driveway/yard. I mean, what haven't i done. I've made so many omelettes that the list of broken eggs is.. depressing. But that's part of why i know so much. Now. Most of the list is from before i was about 22, but i still screw up occasionally. When i'm in teacher mode students often think i'm overbearing when i quick-draw objections to the way people are doing this or that, but i've just become really good at knowing what the lead-up to a mishap looks/sounds/smells like.
Currently living it at Bristol Dragway. It's hot, kid is tired and hot, and they are filming an episode of Street Outlaws....
Eye r dumb.
To continue on the stupid 16 year old trend.
Borrowed (without permission) my dads 69 Covette to pick up a girl I liked from the bus stop (2/3 mile away). She got in and I drove around the side streets in my neighborhood for a bit. Ran out of gas. In my defence who leaves a car with not even enough gas to get to the nearest gas station?
Anywho, thought I stalled it cause I wasnt super awesome at stick yet. After trying to start it a bunch walked home and siphoned out the lawn mowers and my go cart to get a gallon. Battery was dead by this point so no start.
Got 6 neighborhood kids (13-16 yr) and got my riding mower and used the mower to pull while they pushed and the girl I liked steered.
Got it back into the garage with none the wiser.
About a month later the riding mower died (I wonder why) and when my Dad went to the neighbors to borrow theirs the neighbor asked what was wrong with the Corvette. She told him about how she saw me towing it with the mower and though I was towing and he was driving.
All things considered the punishment for that was lighter then what I expected it to be.
When I was about 14 or so I offered to detail my Grandpa's car in exchange for a few bucks--he had a 1970-ish AMC Ambassador Wagon. Green, with "woody" sides. It was a very long car. Very long.
I got it all done, and was very proud of my work, and decided to move the car off to the side of the driveway.
Our driveway was 'L' shaped and had a big iron basketball post adjacent to one side.
I backed into it.
I learned a lesson about not using side mirrors to back up.
I did nothing stupid, with a vehicle, that could be pinned on me. No wrecks, no blown engines, no broken parts. I didn't even have a traffic violation from the time I was 17 until I was almost 42. Aside from getting a few stuck and burning up a few sets of tires, I was pretty tame.
I did start smoking at 16 though. That more than makes up for anything I didn't do with a vehicle and cost me a lot more to boot. It took 30 years to kick that particular bit of stupidity.
Caught hangtime in a 1997 dodge neon. Even bigger hangtime in a 1985 ranger. Both over railroad tracks WHILE a train was enroute. Put my foot out the car door and skidded my shoe on the asphalt at 97mph (speed limiter on cars, no idiot limited on kids), flipped off a cop (ticketed), lied to the cop about insurance, told a cop I got sideways because "I need to get fuel badly", rolled two cars on purpose, passed a car on a one lane road hit a ditch and buried my 1997 neon up to the doors, Fjorded a creek up to the doors in the Fjord ranger, ran nail polish remover as an experimental fuel additive, strapped a buddy to the hood and buried the needle, ate an egg off a greasy valve cover, shall I go on?
Too many to list completely but...
When I was in high school, the restaurant I worked at shared the parking lot with the town mall. Alot of shenanigans went down after closing time, but this particular evening the guys I worked with started to wonder if the studded snow tires on the 68 Camaro I drove, would infact spark on the pavement.
Being up for a challenge (and some hooning) I went out after work about midnight and did some dounuts, a J turn and launched the car as hard as I could spinning the tires in all 3 gears...
Apon returning to my co-workers who were watching by the building I asked "did they spark?" To which the reply was "man... they didn't even smoke!"
"OH... I can make them SMOKE!" I then proceeded to the biggest peg leg burnout... so big that the studded snow tire dug a divit into the pavement that still holds water to this day.
The thing that makes ME feel like an idiot is this...
I had replaced the carb on the Dirtball. While I had it off, I stuffed paper towels down in the plenum to keep random stuff from falling in.
My buddy came over to help me work on the car. I worked on something else, he put the new carb on. The next day I went put to fire it up and it went something like this:
*turn key
-Rrrrerererer
*pump, turn key
-Rrrrrererer
*shot of starting fluid, turn key
-Rerrerrr, Blap!
*two more pumps, turn key -Rrererr blab.. blab..blab..
*More throttle
-Blab blaaaaaRrrrroarrrr!!!!
That is when I noticed the burning shreds of paper exiting the side pipes
There's a road nearby called Rifle lane. It connects 2 fields together, so no houses and hardly any traffic. It's the road we used to drag race on as teenagers.
A recent thread about kids racing in a neighborhood sent me out for a ride last week to see our old strip.
It's half a mile long, sloped, and has a small bridge type thing where a pipe runs under the road near the bottom. I don't remember it being quite so potholed as a teenager, but I do remember catching air in trucks and SUVs racing it the downhill way.
Another fun time, my buddy Ethan went off to basic training and gave me his sound system. So in the back of my 96 Rodeo, I had his 3 12s and my 2 10s connected to a single 800 watt amp, bridged, with berking romex. For the 2 weeks it took before a fire started, any time the bass hit the motor would stumble and the lights would shut off, and I thought it was awesome.
I never claimed to be a genius, but I'll own up to my mistakes. Eventually.
This thread could easily be re-titled, "Teenaged boys are stupid."
When I was 16...I put brake shoes in the front of my 66 Fury II. I took one side off, then kinda forgot stuff, so I took the other wheel off to compare. I made an exact copy of what I saw, which meant the self adjuster was now a self un-adjuster. Several hours later, it all fell apart... on a 66 Plymouth with single circuit brakes. The only answer, of course, was to drive nine miles home down the highway to get to the tools I needed. Reverse is an adequate brake, providing you can coast down to 15mph or so.
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