once a year my best friend’s dad used to wake us up by giving us flu shots. so mean.
10(?), October 1973; again 17 January 1991.
Waking up in the middle of the night to an air-raid siren that really means business is not fun…
My worst ‘waking up’ experience was realising I was driving my car, at about 50 mph, aiming straight for a tree. It was a long, long time ago when I much younger. I had had a few drinks in the pub with friends, safe in the knowledge that I wasn’t going to drive anywhere. Then a very difficult situation cropped up unexpectedly, and I more or less had to embark on a lengthy drive, for someone else’s benefit. I knew it was dangerous and a calculated risk, but I decided that I was sober enough and awake enough to drive with due regard for my own safety and that of others. I was very nearly proved wrong, and was one split second away from wrecking my car and maybe killing myself.
I managed to swerve just in time, and I didn’t come to any harm. Definitely not a good ‘waking up’ experience.
I’ve seen that one. The people they do it to are all fellow celebrities, so it’s probably a set-up.
As for mine, my first apartment in semi-rural Japan was completely infested with spiders and other crawlies that the spiders feasted on. One Sunday morning, I feel a slight itch in my toe. Still nine-tenths asleep, I shrug it off.
tickle-tickle
another shrug.
PINCH!
I jump awake and see a giant freaking centipede with enormous pincers, crawling around the foot of my bed. It was about the size of a fat ball-point pen. I ran to the next room and grabbed a paper towel, and it was still waiting there when I returned. Now, most bugs have the decency to go squish and die when I smash them with a paper towel, but not this thing. It was still alive and attacking the towel! I had to hit it two more times before it finally gave up.
If that’s the worst way I ever wake up, I guess I’ll count myself lucky. I still think John Wayne Bobbit has most of us beat.
Waking up with a mouthful of cold vomit.
Two weeks ago, I awoke early in the morning to my parents pounding down my front door. They’d come over to tell me that my younger sister was dead.
I woke up after the car had stopped. I was hanging upside down in the seatbelt in a smashed car.
I don’t think regaining consciousness is quite the same thing as waking up, for the purposes of this contest. But it’s the OP’s contest so he can be the decider.
I guess it would be worse if it were someone else’s…
The worst case I can remember is pretty tame, really. My kids have seem to despise seeing me take a short nap in a chair (even if there’s nothing else I should be doing and nobody is being harmed). Often they’ll just shout "DAD!’ until I snap awake. One time, my son decided it would be fun to push a long feather up my nose - I woke flailing and panicking, thinking some insect was invading my body.
:eek: 
So sorry for your loss
I hate to say anything after that, but a couple of years ago flying tree branches smashed several panes out of my bedroom window during an early morning windstorm. Had I not had my heavy wooden blinds pulled, I’d have likely been injured and not just rudely awakened.
My dad pouring Alka Seltzer into my ear from about three feet up.
I think he thought it would be funny.
I was so angry I was literally speechless, after the initial gasping yelp of shock.
He can be an ass.
your boyfriend has my empathy. This happens to me regularly as well. Occassionly i will wake up fighting someone/something that is “attacking” me. At least he doesnt remember it.
Not me and maybe not a worst, but a weird: In college, several girls who were looking for entertainment late on a Friday night seized upon an economy sized vat of French green clay facial mud mask, the kind that peels off in a single sheet when cured. They wandered around campus looking for the unlocked doors of known deep sleepers, mostly guys. Said deep sleepers were given free facials while they slept and, in some cases, talked in their sleep. There were some traumatized people who arrived at Saturday breakfast, their first experience of the day having been the sight of their own green faces in the mirror.
The worst was one night, when I’d had terrible insomnia and was sooo happy to finally be asleep, my husband shook me awake to tell me a roach had crawled inside his ear canal.
He wasn’t that happy about it either.
To the OP: “Worst” way? Man, that’s fuckin’ awesome! What did you do to deserve it? 
The OP reminded me of how bad it could possibly get. Being this guy and looking like this in the funny papers.
Tripler
Momma always told me, “Don’t be ‘that guy!’”
Not the worst single time, but it went on every night for three weeks.
My cat started bringing me gifts. First he cleared out a nest of these : 3-5 inches long. He left them on my pillow while I slept. Then he would make a very distinctive mewling sound till I woke up. Nose to nose, they are even less attractive.
Then when I stopped freaking out so entertainingly, he progessed to partially beheaded rats on my slippers.
I think he only stopped because he ran out of prey.
Probably the drunk and stoned guy that tried to open my door, thinking it was his room. When he couldn’t get in he started pounding on the door and yelling obscenities. That was enough adrenaline to last me a few months.
Also, the time when I was in elementary school and the glass light fixture cover thing from the ceiling light spontaneously fell right as I was getting out of bed. It missed me, but apparently my mom was sure that she was going to turn around and see me bleeding to death.
Not mine, I was just a few months old, but our dryer caught on fire when my father was away on business. “Hi sweetheart, I’m at the neighbor’s house with the girls until the fire department finishes” is apparently not an ideal wake-up call.
Phone ringing outside my student room, 7:30 AM, February 16, 1996. I stumble to it all hung over, having come home at about 4 in the morning after a night out.
It was my mom to tell me my aunt had died the night before, at age 49.
That sure was a shite way to start my 23rd birthday.