Coolidge Corner Theatre
Why? No discussion of films in Brookline would be complete without the Coolidge. Whether it's a cult classic played @fter Midnite, or their Science on Screen series, or even a special showing like the Big Lebowski Bowling Party earlier this year, something cool is at the Coolidge.

Brookline Access TV
Why? If you have a movie, and 24 friends to watch it with, you need go no further than Brookline Access TV for a spot to watch. You can rent their 25-seat theatre and watch just about anything there.  
Suggested by: @EricaBATV on Twitter (who works there)

Movieworks
Why? Rentals, purchases, and used movies are available at this independent Brookline store, on Beacon Street near Washington Square. They have deals such as 2-for-1 Mondays, and a $1 store credit for next-day returns. 

Brookline Main Library
Why? For the right price (free), you can borrow the Library's DVD library as though borrowing a book. When you're grabbing some bedtime stories, pick up some pre-bedtime stories for your familes (or post-bedtime for when the kids are asleep). You can also browse the collection online, and rent movies from other locations in the Minuteman Library Network.

Redbox (Located at Shaws and Stop and Stop)
Why? For about a dollar, you can pick up a collection of the latest DVD releases after you've bought your groceries. Stop by the Redbox kiosk in any grocery store (it's usually near the exit, and looks like, well, a red box), watch it for a night, and bring it back the next day.

Keep an eye out for a top movies in Brookline list coming over the weekend.