4. Carrie Fisher: Wishful Drinking (2010)
This is almost cheating because some might not classify it as a traditional movie, but every Star Wars fan in existence needs to watch Carrie Fisher’s unforgettable mix of stand-up comedy and personal documentary. Star Wars fans will of course know Carrie Fisher for her role as Princess Leia Organa at the beginning of the Star Wars films and eventually as General Leia Organa in the sequels.
In 2008, Fisher published a comedic memoir titled Wishful Drinking, but the book itself had been based on a one-woman stage production by the same name which Fisher had premiered in early 2008. After opening at The Geffen Playhouse and having runs in San Francisco, Washington D.C., and Seattle, Carrie Fisher took Wishful Drinking to a limited run on Broadway at Studio 54 from 2009 to 2010.
In 2010, HBO produced a documentary by filming a feature-length version of the stage play, and that’s the film you can now enjoy on HBO Max. The resulting 76-minute film gives fans a must-see look at the life and experience of Carrie Fisher, which is undeniably inseparable from Star Wars.
Wishful Drinking would’ve already found a home on this list on its own merits, but the production is even more poignant and powerful to watch since Fisher passed away in late 2016. It’s a time capsule into her wit, her personality, and her incomparable life that every Star Wars fan should run to HBO Max and experience for the first time, or re-watch even if they’ve already seen it.