1. Planet of the Apes is the winner by far. I refer to the 1969 or whatever version, of course. There used to be a channel in the US that would show the entire five film series for a week or maybe weekend once a year for at least two years and I'd watch more or less that for the duration.
So yeah, the whole series are my top five by a huge margin but I've seen the original the most. Whenever it's on TV I check it out and it's on semi-regularly. The first is the best and they get progressively worse but the fifth is still watchable.
2. Wizard of Oz. Must have seen it 30 times. Shown every year as a kid. It was a big event. And it's shown at Christmas in shitty UK which I also watch. Plus all the odd times it's shown throughout the year.
3. Easy Rider. First saw this on the American Movie Classics or something channel when I was like...25 or so. Just moved back to my creepy mother's house after scam schooling. She was getting a haircut downstairs by her friend's daughter. I still remember the little details like this which happens when something life-changing occurs.
It was great. I couldn't believe that this was shown on American TV. There's no nudity or even profanity but it was so different from any other film I've seen. It really spoke to me. I've seen it dozens of times since. I kept wanting to see it in theatres but my lady friend was never available when it was showing.
4. Christmas Story. Like planet of the Apes, there was a channel that showed this back to back for like a week around Christmas. Hugely popular and it takes place in my hometown. Not Chicago but Hammond. Only film set there that I'm aware of.
Totally unknown in the UK but it's about a boy in the 1950s who wants a bb gun. There's a voice over of the boy as an adult. The film inspired the Wonder Years as the producers freely admit. I don't have the passion for the film as so many others do but I've seen it at least 15 times.
5. Terminator and Terminator 2. I always make sure to catch these when they're on. Best time travel films ever. I don't care about the action sequences but the plot really makes you think.
6. French Connection 2. I must have seen this on TV in the US too. I really liked it and bought the DVD box set with the original but I'm not so amazed by it now. It was the long heroin scene that impressed me. I like the sequel better than the original. Seen the sequel maybe half a dozen times.
Oh. Also It's a Wonderful Life. Seen it loads. Twice in theatres. It's great. I don't want to edit my list any more but this should probably be number...4.
That's all I can think of offhand. Films I've seen at least six times...there's maybe a classic I'm not remembering.
Honourable mention for NOT watching Home Alone. It's on all the time in this shit country and of course it was huge in 1992 or whenever so it takes effort to avoid it. But I hate that little homo so shun this shit. I think I've seen the third one where it's a different (Jewish) kid but never the first two.