I don’t usually respond to these prompts, but this seemed fun. First up, TV series:
Star Trek Deep Space Nine. With the other Trek series, I generally pick and choose episodes. Yeah no, I’m not watching “Spock’s Brain”, “Code of Honor”, or that one Voyager episode in which Jeri Ryan is a cage wrestler fighting The Rock. (shudder) But Deep Space Nine, I love me some Deep Space Nine. It was the first Trek series I owned all the sets for, and whenever I want to go to sleep listening to Trek I always pick DS9.
Boy Meets World. The first DVD set I ever owned was the first season of Boy Meets World. I grew up with this show, so it’s incredibly special to me. I even use the season 4 opening theme as my oldest niece’s ring-tone because it was one of the things we watched together when she was a wee bairn and I was her babysitter.
Survivor: Borneo and Survivor: All-Stars. Don’t judge me, it’s a nostalgia thing. Borneo is really interesting because it was the first series, with the rules still being made, and All-Stars was the peak of my Survivor fandom; I stopped watching not long after, in part because of college and in part because once you’ve seen Boston Rob in All-Stahs there’s really nothing better.
“….what’d y’all order a dead guy for?”
“Well, look at this! Seems we arrived just in the nick of time. What’s that make us?”
“Big Damn Heroes, sir.”
“Someone ever tries to kill you, you try to kill them right back!”
“Your mouth is talking. You may want to look to that.”
“May have been the losing side. Still not convinced it was the wrong one.”
“Mercy is the mark of a great man. (stab) Guess I’m just a good one. (stab) Well, I’m all right.”
Firefly. Not sure how many times I’ve watched this. Right after college I watched two clips from Firefly‘s pilot and was instantly hooked. The first was Wash doing his dinosaur thing (Ahh! Curse your sudden but inevitable betrayal!) and the second was Kaylee twirling her umbrella. I was hooked instantly, bought the DVD set, and have watched it continuously since.
Breaking Bad. Whenever I’m dogsitting for someone and realize they have Netflix, I just watch Breaking Bad. Better Call Saul will definitely earn that in time.
The Office (US) if we’re just counting the Michael Scott series. I can enjoy seasons 8 and 9 but I don’t watch them regularly.
Movies:
Hmm…
The Sandlot, definitely. No question. West Side Story, I watched 5 times in fourteen days in 2004 and have watched every other year or so since. The Philadelphia Story and Groundhog Day have been once-a-years for the last 15+ years, and Lemony Snicket’s Series of Unfortunate Events is not far behind. Contact, the original Ocean’s Eleven, and a few others are regular. For Star Trek, I know I’ve seen The Wrath of Khan, The Voyage Home, and First Contact more than five; for Star Wars, I used to make an annual habit of watching the original trilogy and then the sequel trilogy between Thanksgiving and Christmas. I haven’t followed that tradition for a few years but I’m sure I’ve seen them all at least five times or more. I’m sure there are many other movies that qualify: The Lion King and Home Alone, for instance, are movies I’ve seen so many times I can’t really give you numbers for. Not sure where the Harry Potter movies fall: I’ve seen the earlier ones several times, the later ones only once at best. Prisoner of Azkaban probably has the most re-watches because I will never get tired of watching Hermione punch Draco.
Reading Freely 
I *think* my record for re-watching is the original ‘Bladerunner’ at over 60 viewings…. I don’t think I have anything else anywhere *close*. Probably next up after that would be movies like ‘Zulu’ and ‘Where Eagles Dare’.
That is…impressive. Where Eagles Dare is that Eastwood/Burton film with the Nazi mountain fortress, right? Watched it several times in high school. Fun stuff — Broadsword calling Dannyboy!
Just noticed I need to make an edit….I watch the prequel trilogy, not the sequel. I was so disgusted by VIII that I never bothered with IX.
Yup. ‘Eagles’ is that one. Very silly (esp the helicopter!) but LOTS of fun.
Ep IV was ok, just…. After that I lost a lot of interest in all things SW. The only one I *really* liked was ‘Rogue One’. It’s the only SW movie I own on DVD and probably the only one I’ve watched multiple times..
I did like Rogue One, yeah. I even enjoyed Solo, or at least his friend-who-betrays him. Kira or something..