I'll do more than 10 times just to narrow the list quite a bit... and I'll also add these were watched start to finish... example, I've probably seen some stuff like Ferris Bueller's Day Off and Shawshank 25 times, but it was almost always on TV and rarely ever from start to finish. Some of these I saw a bunch of times many, many years ago. Others are guilty pleasure type movies that I'll watch once a year or so. What this isn't is a list of critically acclaimed movies (for the most part).
Major League
Field of Dreams
Back to the Future
Ghostbusters
Office Space
Top Gun
Road House
Old School
Billy Madison
Howard The Duck (don't judge too much here, but when I was a kid and I found Showtime, this movie was on every day for abut a year)
Fright Night (see also: Howard The Duck)
Gremlins (again, a regular Showtime watch in the 80's as a kid)
Four Christmases
Christmas Vacation
Vegas Vacation
Caddyshack
Meet the Parents
Wedding Crashers
Step Brothers
Dumb and Dumber
The Hangover
Opportunity Knocks
Coming to America
Karate Kid
Die Hard
Lethal Weapon
Fletch
Airplane
The Great Outdoors
The Patriot
Tombstone
Young Guns
Open Range
Maverick
Full Metal Jacket
Also, there's several kids movies that I watched many, many times with Little Miss. Van de Graaff in her earlier years like Frozen, Ice Age, Finding Nemo, The Incredibles, etc... easily 10+ times.