*MINOR SPOILERS*
Juno
I honestly love anything with Ellen Page, but Juno is one of my favorite movies ever. Besides the obviousness of the dialogue having been written by non-teenagers at points ("honest to blog?"), this movie has almost no flaws. The story is heartwarming, funny, and of course, emotional. Not to mention, Kimya Dawson, The Velvet Underground, and The Moldy Peaches are all featured on the soundtrack.
Plot in one sentence: Teenage girl gets pregnant with Michael Cera's child.
Scene that makes me cry the most: Juno and Pauly in the hospital bed after Juno's birth.
Perks of Being a Wallflower
If you haven't seen this movie by now, then you never had that friend who wore beanies or browline glasses and said things like "I love feeling this free" while walking around town late at night. This film tackles everything from mental illness to homophobia, so get those tissues ready because we are dealing with some deep subject matter. While cringe-inducing at some parts (yes, I'm talking about "welcome to the island of misfit toys"), it is an all around great movie about friendship, mental illness, and high school.
Plot in one sentence: Introverted freshman befriends a group of kind seniors at his high school.
Scene that makes me cry the most: Charlie's phone call to Mary Elizabeth after breaking up: "Tell it to someone who cares, Charlie."
Little Miss Sunshine
Probably my favorite role of Steve Carrell's career (besides Michael Scott), this movie beautifully depicts family dysfunction. Little Miss Sunshine is a great movie to watch alone, so you can sniff and sob all by yourself as you watch little Paul Dano and Abigail Breslin act their hearts out. This movie is hysterically funny, but also incredibly emotional and raw.
Plot in one sentence: Family goes on a road trip for daughter's beauty pageant.
Scene that makes me cry the most: Dwayne finding out he's color blind.
The Way Way Back
You might think I have a thing for Steve Carrell, but it's just a coincidence that he graces us with his great acting in this movie too. Starring Liam James in a breakout role, this movie chronicles an awkward teen's summer vacation with his mom and her asshole boyfriend. While I really love The Way Way Back, I must warn you that it will make you sad you never worked a summer at a waterpark with a bunch of cool adults.
Plot in one sentence: Socially inept teenager works at a waterpark and blossoms into only half awkward.
Scene that makes me cry the most: Duncan being told his dad doesn't want him to move in.
Good Will Hunting
I'm sure you seen this movie or at least fibbed at one point said you had. Matt Damon and Robin Williams are cast perfectly in this picture that tackles mental illness, abuse, trauma, and self-love. The title character, Will, has to work through the hardships of his past in order to move on and to love and trust others. Don't watch this movie if you aren't ready with three boxes of tissues and four tubs of ice cream.
Plot in one sentence: Genius Janitor is forced to study math and go to therapy.
Scene that makes me cry the most: The "It's not your fault" scene.
Submarine
Ah, young love...or rather, young 'I like you and want to hang out with you more'. Submarine perfectly captures the weirdness of liking someone seriously for the first time and trying to act like you have it all figured out. It is partially reminiscent of Perks in the sense that these kids are quite artsy and maybe unrealistic depictions of high schoolers, but are lovable nonetheless. This movie isn't an incredible cry fest but may make you tear up a little bit.
Plot in one sentence: The story of two high schoolers dating (?) each other.
Scene that makes me cry the most: Oliver seeing Jordana with another guy.
The Outsiders
Yeah I know... You've already seen this movie. However, if you are reading this article and really do need a good cry, at least you can do it while looking at Rob Lowe, Patrick Swayze, and Tom Cruise. This movie is obviously a classic and the novel is just as good if you have some time on your hands.
Plot in one sentence: Group of misfits witnesses a death of an opposing gang member.
Scene that makes me cry the most: "Stay gold, Ponyboy"