It’s Wednesday night and you’re in the mood for two things: Leonardo DiCaprio and your vibrator. Only one problem: You’re not some basic bitch. You could go the easy road and jerk it to Romeo + Juliet, or you could be a fucking trailblazer and jerk it to Revolutionary Road. After extensive research on behalf of our senior masturbation editor, we present to you with pride: the definitive ranking of Leonardo DiCaprio movies that are the hardest to masturbate to, from medium-hard to experts-only.
Since this list is more about difficulty masturbating to Leo, Inception ranks toward the easier end of things. Lots of suits in this film, a lot of brooding, a lot of Leo wet on a beach. You can easily climax to the thought of him hitting you with his train.
Mental illness and period costumes are not a great orgasmic mix, but you’ll figure it out. There’s a scene in Shutter Island where Leo is hanging on the edge of a cliff and you’re not sure if he’s going to make it. The tangible fear in not knowing the fate of your beloved is enough to bring you to orgasm, if you really work at it. This movie is a bit heavy and not particularly sexy, but with the right vibrator it won’t take you very long to come from this crazy cutie.
The 1950s male fashion is really what gets me off here. The suits and the combed hair and the pulled-together look. Lots of men with repressed feelings, and I don’t know about you, but nothing makes me squeal harder than Leo repressing his emotions to the point of total self-destruction. I’d say, however, you definitely need a vibrator, on the highest setting it can be, to get you through the unspeakable sadness of love’s slow decay.
I have not yet seen all of The Revenant, but let me tell you, it only takes watching the trailer thrice to reach optimum masturbation success. I did need to get creative… there was a lot of nip-touching and lube… and the bear scared me… but it worked. Def recommend skipping the bear parts and most of the middle of the movie.
Gangs of New York
Leo wears a lot of cute Newsies-type outfits in this. The hair is a good length, good goatee, plus a fistfight! I’d say you best bet for this movie is to put it on mute while you lube up your vibrator and honestly? Don’t be afraid of a little butt play. A pinky is fine. But the accents are really hard to get past, and Daniel Day-Lewis’s acting is so good that you’ll get stressed out.
This is where things got way harder. Celebrity is a black-and-white Leo movie that I haven’t fully seen, but from the clips on YouTube I gathered enough to form a movie in my mind. I learned that if you use enough lube and finger yourself at the right angle, eventually something will happen and you can turn this shit off.
Honestly, I was so consumed by the powerhouses that are Diane Keaton and Meryl Streep that Leo was the last thing on my mind. I just held my vibrator against my clit for like an hour and finally something happened. Idk…
It’s hard to focus on anything else except that awful mustache. You’ll need a really good vibrator for this one. Possibly two vibrators. Basically, what I’m saying is it’s going to take you so long to get off to this that you’ll wear out the batteries on one vibrator and need another one to finish the job.
The Quick and the Dead
Leo is close to a fetus in this movie. Honestly, I had to close my eyes and it took a lot of vibrator/nip action to get me where I wanted to go.
I’m not really a fan of Tarantino (it’s hard to masturbate when you can’t get past all the blood on screen), so I didn’t watch this movie. I did, however, masturbate to a photo of Leo on the set of the movie. That took a long time though, because it’s really blurry. Pretty sure I had an org but unclear, could have just been a weird muscle thing.
What’s Eating Gilbert Grape
Listen: I tried and I don’t recommend it.
The bottom line is all of these movies, sans the last one, can be masturbated to. It might take a bit more work for one versus another but at the end of the day, Leo is so so worth it and your vagina will be happy. And isn’t that all that really matters?