25. Friends With Benefits (2011)
Friends With Benefits, which revolves around an agreement between two new friends (Mila Kunis and Justin Timberlake) to enjoy completely emotionless, commitment-free sex, manages to deliver feel-good vibes minus the nauseating clichés (well, for the most part).
One of the film’s coups is that the sex in this semi-alternate rom-com universe is actually funny in itself, not in a slapstick way, but in an honest way. During one of the pair’s earlier care-free sex sessions they both go down on one another. While Timberlake needs a tiny bit of coaching, Kunis is an undeniable pro, leaving her partner quite speechless. If this, plus ample shots of a half-naked Mila Kunis weren’t enough to merit a little more than two thumbs up, the film can likely be credited with the emancipation of guys the world over from the confines of the dreaded friend zone. Not a bad deal.
24. What’s Eating Gilbert Grape (1993)
In the fictional town of Endora, Iowa, Johnny Depp plays a family man named Gilbert Grape who’s left in charge of caring for his mentally challenged brother Arnie (Leonardo DiCaprio), his sisters, and his morbidly obese mother. Given the material, it would have been easy for Depp’s titular character to just be seen as a bit of a weirdo, yet Depp digs his heels in and imbues some subtle nuances into the character that make his relationship with his family that much more engaging.
In the midst of all of this, Gilbert is having a secret affair with a housewife named Betty (Mary Steenburgen), while her busy husband (Kevin Tighe) tries to sell his family life insurance. In the ultimate slick willie move, Gilbert gets a BJ in the kitchen while he’s reluctantly talking to Betty’s husband on the phone. This particular scene is memorable for its awkwardness as much as its hotness.
23. The Basketball Diaries (1995)
Based off of the novel of the same name by the famous poet, Jim Carroll, The Basketball Diaries is not your average basketball movie. You’ll find no clichés here about the game and its ability to help people rise from unfair circumstances, instead, the film explores drug addiction, sexual abuse, and a number of other uncouth realities.
Two years before he became the world’s biggest stowaway-turned-heartthrob, Leonardo DiCaprio was dealing with sex, drugs, and cancer in this gripping drama. One of the most distressing moments of the film is when DiCaprio’s character, desperate for money to feed his drug addiction, whores himself out and receives oral sex from another man in a dirty public bathroom. It’s a moment that adds to the film’s theme of what we have to do when reality begins to encroach upon our dreams. And it ain’t pretty!
22. Carrie (1976)
Poor Carrie White, she never had a chance. Her mother was a religious nut, her father wasn‘t in the picture, and she’s agonizingly shy. Things at school aren’t much better, she’s customarily bullied and treated like a freak. She also struggles with the realization that she posses telekinetic powers. However, we’re lead to believe that Carrie’s luck has turned around when she gets asked to go to the prom, and you couldn’t be happier for her.
It slowly dawns that there’s a cruel prank planned. But first one of one of Carrie’s tormentors, Billy (John Travolta), needs a little convincing to get involved in the shenanigans. To put it bluntly, his girlfriend proceeds to blow him in his car as she proceeds to say over and over again “Billy…Billy…oh Billy…” How does she continue to speak while her mouth is full? Who knows. But needless to say, he becomes convinced.
21. Casino (1995)
Casino, the second collaboration between crime reporter Nicholas Pileggi and Martin Scorsese, who first joined forces to adapt the writer’s 1985 non-fiction mob account Wiseguy into the 1990 Academy Award winner Goodfellas, will always live in the shadow of the gangster classic that preceded it. But then, so do all movies that have followed what is arguably Scorsese’s masterwork.
One of the most iconic aspects of Casino is Joe Pesci as Nicholas “Nicky” Santoro, a mob enforcer who sticks a guy’s head in a vice, stabs an unlucky bloke in the neck with a pen, and in one classic scene, gets head from a showgirl (Shellee Renee) in the parking lot of his restaurant. Oh, and he also gets blessed by Sharon Stone’s character, Ginger… like a boss.