re: Dr Thumb
Dr Thumb had an unfortunate genetic mixing that left him without facial distinction. I’m not sure how to describe this other than as follows:
Take the ball of your thumb.
Draw eyes on the ball between the point of the ball and the nail.
Draw a mouth underneath the point of the ball of the thumb.
Wiggle it up and down and pretend its listening to you or explaining academic policy.
At a company I worked for between '99 and '01, I discovered that there was no shared calendar, and your boss never really knew if you were in a meeting or not. So one afternoon me and this girl who also worked there vaguely mentioned an offsite meeting to our bosses, then we walked up the street and snuck into the movie theater. It was the original release of The Sixth Sense, a movie I knew nothing about, and it got me, completely.
Another time about five years ago I broke my elbow and got a coworker to drive me to a contractor meeting a couple of hundred miles away on the coast. We had a company rented vehicle and the meeting was in the morning. We spent the rest of the day with me saying “left” “right” or “straight on” at each junction, and her driving us around the coast, then went for a long pub lunch and had a long walk on the beach. Lovely day out.
(I do actually work hard and do long hours, but those were the two Bueller moments of my career.)
Yes I have. Early senior year in high school. Several laws were broken (no one was hurt or stolen from, unless they deserved it - the stealing from I mean) and I am STILL not talking about it.
I was going to say no… I was the kid with the best attendance record in school (I remember my mother shrugging and telling me ‘You can die at school just as well’ when I was ill), but yes- really, I did, just with my Dad’s permission.
I went to Glastonbury festival, (without a ticket- got in through a hole in the fence), when I was supposed to be at school.
My mother was pretty furious when she discovered my plan, but my Dad had the attitude that I was over compulsory schooling age, and if I wanted to do it, he saw no reason why I had to go to school for the day if I didn’t want to, and even wrote me a sick note afterwards. The school was normally really strict on it- even at 17, I wasn’t allowed into town on free periods (though I did slip out to the city library quite a lot as well).
A friend from a different school said her head teacher had announced to everyone that he was going to be watching the 24hr Glastonbury footage on the BBC, and any student seen on it was automatically suspended. But I went to the goody-two-shoes school, and no-one thought to check. 
I was planning to buy a ticket, and had saved up enough, but I was going with a friend (who was at art college, and had no worries about taking time off), and she turned out not to have the money last minute, after we’d already bought train tickets, so I thought we’d trust our luck together, rather than have her stuck outside, and it’s such a vast site, trying to find each other even if she did get in could have taken most of the weekend, and we only had one tent.
I can safely say I learned a lot more in those few days (I took thursday afternoon- when I had no classes anyway but was supposed to be on the premises- and friday… and inadvertantly monday as I was on the edge of collapse when I got back) than I possibly missed. 
Best ‘unpleasant stomach upset’ I’ve ever had- thanks Dad!
Had a work version:
Working in the “office” part of a clinic department, you often tend to be separated from the clinic staff. This particular clinic staff had a history of poor morale, poor interactions, etc. and to keep things functional, managers tried to do things to make the clinic staff happier and/or not want to kill each other. Often the office staff got forgotten in things like pizza ordered in for lunch by the managers, etc., because they were few and got along well. This, not surprisingly, did not help the morale of the office staff.
One Friday I saw clinic staff with special T-shirts on. Appreciation day t-shirts. And they got breakfast brought in by the managers, and flowers, and balloons, and lunch paid for at a nearby restaurant.
Not us, though. We didn’t even know about it. We were pissed.
My coworker (who I shared an office with) and I were done with our patients at 1:00. We had a conference call with one of the doctors and a pharma company at 3:00. We also had cell phones and the conference call info.
We clocked out and headed out for lunch, then split up for shopping (Chicago, so this is good dining and shopping opportunity here). Conference call went off without a hitch - I parked myself in the lobby of an office building next to a Starbucks entry - then I met my husband for our planned night on the town and confessed our little afternoon off. He was worried that we’d get in trouble. Finished off the night with a movie in a theater just off Michigan Avenue, then lots of margaritas and Mexican food, and semi-slurred bitching about the treatment.
The following Monday or Tuesday, we got a half-apology and attempt at justification, a paid-for lunch, and no mention of the early departure.
I did skip my high school’s unofficial senior skip day, after swearing up and down for my first three years that I was going to be one of the diligent kids who went to school anyway and enjoyed the nearly empty classrooms. Nope. Slept in and worked on some homework assignments, then went to the pet supply store with my mom to buy cat food and spent the rest of the afternoon with the cat playing with the new toy we bought at the store.
When I was a freshman the administration was not very strict, and during exams week I would skip classes that had no final exam to hang out with my senior friends who had already graduated.
Some friends and I skipped the senior picnic and ate at a nice restaurant instead. Unfortunately I was pretty boring in high school.
My uncle had a Ferris Bueller’s day off, and he spent the day in the skate park with his best friend.
He totally would have gotten away with it, too, if the hospital bill hadn’t come in the mail two weeks later.
Does spending nearly my entire third year of law school counting cards in Atlantic City count?
Never skipped a day of school in my life. Senior year, I actually begged my mother to go to school so I could be sent home by the nurse. I had a 104* fever and no voice…this was all done via notes…needless to say, I missed 4 years of perfect attendance by one day. 
Worst I can say is that I called out of work when we had an ice storm when I lived in Mississippi…I lived 30 miles from the office and the roads in my town were icy. We also lost power, so it was legitimate…
Not a skip day–school sanctioned trip.
I went with my Chemistry class to some sort of event at a local college campus. I don’t really recall the details, and it was generally a nice change of pace to school, but not especially awesome.
The memorable part is that my face turned up in the paper–practically life-sized the next day. Apparently I had been standing next to one of the young men who was being followed by the paper for a series on helping the underprivileged (or something like that). So they printed his name in the paper, but not mine. Which was fine–I was seen by quite enough people as it was.
Being kind of a late developer I did not have the epic day off until I was in college, and it was the occasion of my 18th birthday.
I had never had to go to school on my birthday before (summer) and didn’t think I should start then, but it wasn’t really ditching in college, so it probably doesn’t count. We didn’t have to elude truant officers and we didn’t have to steal the Corvette, nor did we wreck it. Great day.
The only thing that could have made it better was leading a group singing “Twist and Shout” but that didn’t happen either. Instead we finished off by going to a folk concert.
Well, I once went on a school-sanctioned trip where the CHAPERONE took a Bueller… week, actually.
A group of cadets from the military academy where I went to high school took a trip to Chicago for spring break. The faculty sponsor that went with us gathered us all in a hotel room the first evening and said that he thought we were all basically adults, he trusted us not to do anything that would attract the attention of the authorities, and if it was all the same to us, he’d prefer to just stay in his room and drink all week while we ran around Chicago unsupervised. We agreed that his plan seemed sound, and put it into practice immediately.
I never skipped a day of school until I got to college. Once I started missing days in my junior year it was only a couple of months before I dropped out entirely.
When I was younger I played hooky from work quite a bit. One time I called in sick so I could go stand in line to get concert tickets. Another time I called in from a campground pay phone, having spent the previous night at Henry Coe State Park.
In our senior year we planned a ditch day ahead of time and went hiking up in the mountains. This was in Hawaii. It was magical! We all had extra curricular activities so we were not meant to be back at school until around 6 pm when we got picked up by parents or whatever. So we had the whole day.
We hiked to a waterfall and hung out there all day. There were about ten of us. It was a beautiful day and the nature was astounding, with great company to boot. Like I said, it was a magical day, though I still shudder at the thought of all the things that could have gone wrong for us. It was incredibly dangerous, looking back. This was before cell phones, too. And we were jumping off rocks into the pool the waterfall crashed into.
We could easily have been the subject of one of those Discovery/National Geographic channel sensationalist rescue shows! There were no accidents however and it was one of the happiest days of my adolescence.