The original Blues Brothers movie. That’s one that never gets old, and I’ve seen it at least once a month since I got the DVD when it first came out.
Could be Spaced Invaders for me. I loved that flick and I saw it many, many times in the 90s. I am pretty sure that few other people have seen it.
I watch The Goonies, uh, frequently. I throw on the BluRay at least once a month, usually more. In the last few months I’ve been playing on an old VHS tape on a TV/VCR combo we pulled out of storage and set up next to our video game setup. Even more frequent now.
Yes, I have it all memorized. No, I don’t know how many times I’ve seen it, 150, 200? Maybe. Sometimes it’s just on in the background while I clean, cook, or wrap presents. Sometimes I don’t finish, sometimes I start it randomly somewhere in the middle like I caught it on TV.
Back in the mid-80s, I think I saw “Streets of Fire” pretty much every time it came on (either Showtime or HBO, I don’t remember which). Cheesy dialogue and iffy acting, but I loved that movie.
I’ll concede the number of times watched title to you, but this is my favorite movie. I tried to make “You’se fancy-pants, the lot of ya” a part of my vocabulary, but it’s a hard phrase to work into a conversation. I have had a little more success with “Maybes don’t make it so” and “Ain’t it the life, though”.
Way back when, one of the Starz channels ran the same 4 films over and over everyday in the same time slots for a week. One of the movies they like to cycle was 10 Things I Hate About You.
Sometimes I’d leave the TV on this channel just for background. So I’ve “seen” that movie a remarkable number of times. Larry Miller as the dad makes all the difference, I tell you. 
Larisa Oleynik was quite good in this. But practically the only thing I’ve seen her in since is a batch of Mad Men episodes as Cynthia Cosgrove. (She could have married someone better. But then you could say that about nearly all the women on that show.)
OTOH, there have to be die-hard Heath Ledger fans that have really watched it a ton.
According to an article in Slate, Tom Hanks has seen 2001: A Space Odyssey more than 200 times. I wonder how many times he’s watched his second-favorite movie? 
I will fight anyone who claims to have seen Beastmaster more times than I have! (Another movie I haven’t watched in 30 years because I’m quite certain that it’s terrible.)
I’ll take that bet. I watch it a few times a year now but in the 90s (when I was single and had nobody to answer to) I watched it a couple times a month.
I don’t know. Had it on VHS. My friends and I watched near daily for 2 years while stationed in Germany.
“So many assholes, so little bullets”
I have seen planet of the apes many many times over the years.
I am talking about the Charlatan Heston version.
Probably not a world record, but I’ve seen the underappreciated Top Secret! (a lesser known effort from the makers of Airplane!) at least 25 times.
Oh, the fake version! With the lower-case primates.
I’m sure I haven’t watched it more than anyone alive, but I’ve seen the original King Kong a hell of a lot of times. In New York in the 1950s Million Dollar Movie used to show the same old movie every weeknight for a week, and three or four times back to back on Saturday and Sunday starting early in the day. Whenever King Kong was on, I would try to see it as many times as possible during the week and weekend.
I had to give this some serious thought. I just might make a case for The Mothman Prophecies (2002), but only because it was crummy and not many people watched it at all. (It does appear that it grossed about $55M worldwide, but I find that shocking to contemplate.)
Anyway, it was on HBO and so my wife and I sort of ended up seeing it a couple times by accident. Then we went on a 10-day cruise where it was one of only a few movies in rotation on the shipboard channel. After we got back, it just sort of popped up all over the place and it reached the point that we would deliberate turn off the TV to get away from it. So, all told, I’ve seen it probably 25 or 30 times. And it has sucked every single time.
I’ve seen Silverado at least 120 times and probably closer to 200 I still watch it 4 times per year. I’ve named my dog after the movie.
As a young teen in the 80s, I had a HUGE crush on Lea Thompson. I know I’m not the only one, and while I’ve watched the Back to the Future movies dozens of times, I know others have seen them more. Likewise Red Dawn, All the Right Moves, Some Kind of Wonderful, etc.
But SpaceCamp… I might be in the running for that one. It helped that not only was I in love with Lea Thompson, but I was also really interested in astronauts and the space program. I saw SpaceCamp in the theater at least three times, then when it started showing on HBO multiple times a week I would watch it every chance I got. Eventually recorded it on VHS and proceeded to wear out the tape. Bought the DVD years ago and have watched it dozens of times. I know it’s not a very good movie, but it’s ‘comfort food.’ Takes me right back to those more carefree days.
As have I, I’m guessing around 50. Also high on my list is Caddyshack and Mad Max.
Surprisingly, I wore out a VHS copy of The Gong Show movie. Seen it around 70-100 times.
But the granddaddy is Collateral. I’ve seen it over 200 times.
When I was in high school I would watch one act of the Woodstock movie every morning while getting ready for school. I don’t know how many times I’ve seen it but it has to be a lot.
As I said, I only watched it because my son from the age of 3 - 6 watched it at least daily. And you are correct it was terrible. But in a little boy’s mind it was amazing! When I think back, it was probably quite inappropriate for a kid of that age! Oh well…
There’s a number of Dopers who think it’s great.
Yeah, but you’d have to have seen it hundreds of times to have seen it more than anyone. There were plenty of hardcore fans who went to the midnight showings every Saturday for years, all dressed up as characters and stuff.
I can’t think of any movies I might have seen an extraordinary number of times. Duck Soup (of course) and Monkey Business, a couple dozen times each. Casablanca and Maltese Falcon, maybe a dozen times each. Ditto Monty Python and the Holy Grail. More than the average in all cases, but way less than some fans.