If there’s one thing geeks know, it’s which movies show the “slightly-off” guy getting the girl. And who better to play guys who are just slightly off than John Cusack?

With that in mind, here are six of the best John Cusack romantic comedies, keeping in mind that I haven’t seen everything he’s ever been in so I might have missed your favorite:

6. Hot Tub Time Machine Let’s start with the most recent of the bunch, in which John Cusack* and two of his friends (and his nephew) go back to the 80s (Cusack’s best decade, in my opinion) to relive history… and change it. Honestly, Cusack doesn’t get the best lines in this film — those go to Rob Corddry and Craig Robinson, and even to Clark Duke at times. Plus, other than the bits with Corddry at the end of the film, the ending itself is a bit saccharine. Still, for anyone in the 2000s jonesing for the Cusack of old, this was a good entry.


5. High Fidelity Based on the book by Nick Hornby, this film is about John Cusack owning a record store** and trying to figure out how he keeps screwing up his relationships***. Really more about the monologuing than anything else, Cusack was praised by Hornby in the role, even though it’s hard to believe anyone, even in 2000, could make a living owning a record store.

4. One Crazy Summer This film is a bit of a departure in that sports are involved. Specifically, Cusack is a basketball player who wants to be an artist and to do so he has to write and illustrate a love story. Demi Moore of all people plays the love interest… but then, it was 1986. Bobcat Goldthwait and Curtis Armstrong steal a lot of the show, and it’s been a while but I do remember there were some cartoon moments as well that were vaguely amusing. Again, the plot was fairly simple, but I liked the movie.


3. Say Anything Some call this the iconic John Cusack movie. He plays Lloyd Dobler, a guy who seems to be fully self-actualized and not afraid of going for what he wants. He wants to date Diane Court, so he asks her out. Things, unfortunately, don’t go as well as they could. This film has several iconic scenes, including the pen scene, the boombox scene, and even the scene on the airplane at the end (which I thought was a great way to end the film). As usual, the cast includes Jeremy Piven, who is Cusack’s friend in real life.

2. Better Off Dead Oh, where to begin, where to begin… Released in 1985, this film was a staple of Comedy Central in the early 2000s. I’d never seen it any other way, so when I finally got the DVD and saw all the stuff that Comedy Central had to cut for time, I was blown away. It’s truly a black comedy, and one of the top 100 films I’ve seen, in terms of enjoyment. This one features John Cusack as Lane Myer, whose girlfriend breaks up with him. He falls for a pretty exchange student, fixes up his car, drag races two Japanese guys, and eventually has to ski against his ex’s new boyfriend for some reason. Featuring Curtis Armstrong as Cusack’s best friend and Vincent Schiavelli as a teacher in one of the strangest classes I’ve ever seen on film, Better Off Dead can still make me laugh out loud.


1. Grosse Pointe Blank John Cusack graduated high school, went into the military, left the military, became an assassin, and is now back for his ten-year high school reunion. Jeremy Piven is there. Minnie Driver is the love interest. Dan Ackroyd is a delightfully-insane bad guy. Alan Arkin, Hank Azaria, K Todd Freeman, Carlos Jacott, Mitchell Ryan, Jenna Elfman, and even Cusack’s other siblings appear (including Joan Cusack in one of her best roles since Toys). My best friend took me to see this for my 19th birthday, and it made a huge impression on me. I love this film. Why? Here’s six reasons:

  1. “You don’t get to have me!” — my favorite line ever delivered by Minnie Driver.
  2. The sheer absurdity of a hitman attending his class reunion.
  3. Marcella as Cusack’s secretary.
  4. “I killed the president of Paraguay with a fork. How have you been?”
  5. The girlish glee on Minnie Driver’s face in the “airplane” scene.
  6. “If I show up at your door, chances are you did something to bring me there.”

If you only see one movie on this list, see Grosse Pointe Blank. Especially if you missed out on your high school reunion, as I did. I’m sure Martin Blank’s was better anyway.

Bonus Content!

Want to see something crazy? Actor Chris Marquette looks very much like a young John Cusack. I wonder why they haven’t ever been on screen together.

Got an idea for a future “Six of the Best” column? Tweet it to me @listener42.

* Yes, I know, that’s not his character’s name. But in romantic comedies he basically plays the same guy every time.

** I know, right?

*** I know, right?