My Top 5 John Cusack Flicks

JohnI’ve lost track, Modern Philosophers, of how many times people have stopped me on the street to ask me what my favorite John Cusack flick is.

I had the interns keeps track for a while, but I get a new batch of them every semester, and the tallies always seem to get lost.

Since I’ve been looking for new features for the blog in 2015, I thought I’d publish my first Top 5 and make it a list of my favorite John Cusack films.  I know there are other lists of top movies starring this actor, but you can trust that this is the definitive one.

The Sure Thing1. The Sure Thing gets top billing on the list, and I know that is going to surprise many of you who haven’t even heard of this flick.  Trust me, this is Cusack at his finest.  He is so young in this movie, but perfectly cast as the cocky kid who goes off to an Ivy League college and then has to hitch a ride cross country so he can get laid in Sunny California on his Christmas Break.

The movie is directed by Rob Reiner, and features a classic scene about hitchhiking that still cracks me up every time I watch it.  Even though the premise sounds very unromantic, there is a sweet love story that this Hopeless Romantic simply adores.

It’s his best flick.  Watch it if you haven’t.  As an added bonus, John will teach you about Cassiopeia and show you how to properly shotgun a beer.


2. Serendipity is a movie I will watch anytime I stumble upon it while flipping through the channels.  I always associate it with Christmas because of the opening scenes, and I was so pleased to find it on cable over my Christmas vacation.

This is another romantic comedy that plays right into my wheelhouse because it explores the place fate and signs play in finding your true love.

The supporting cast really gives this one a bump up the list.  Kate Beckinsale is so beautiful and charming, and frequent Cusack costar Jeremy Piven is a hoot.

If you’re ever at a point where you’ve given up on finding the love of your life, watch this movie and your faith will be renewed.

Ironically, John once again teaches us about Cassiopeia in this one.

Bonus points for being set in New York!

Say Anything3. Say Anything… I don’t even need the movie poster for this one.  You see that iconic photo of John in the trench coat with the boom box held over his head, and you know what the flick is.

I’m sure many of you will argue that this is the best Cusack film out there, but I say it’s too much of a downer at times to snag that top spot.  Plus, the ending really is annoying.

Lloyd Dobler is the greatest Cuscack character of all time, though.  Cameron Crowe deserves major props for his writing and directing.

I gave her my heart, she gave me a pen.” — Lloyd’s most memorable line.

I called her up.” — Lloyd’s awesome response when asked how he got Diane Court to go out with him.

I’ll never hear “In Your Eyes” and not think about this film.

Con Air4. Con Air That’s right, Modern Philosophers, I’m jumping off the romantic comedy bandwagon for the fourth spot on the list.  Sometimes, a guy just needs an adrenaline fueled joyride on movie night.

Sure, Cusack isn’t the main character in this one, but that’s his name and face right there on the poster of an action flick with an All-Star cast.

Who doesn’t love a movie with dialogue that’s as kick ass as the action?

better off dead5. Better Off Dead I’m totally blowing your minds with this one, aren’t I?  While probably even more obscure than The Sure Thing, it’s also freakin’ hilarious.

Another flick starring a very young John Cusack, it’s a romantic comedy with a suicide subplot, which makes for some very dark comedy.

This one is memorable for Curtis Armstrong in the sidekick role, the paperboy with a blood thirst for this two dollars, and the Japanese drag racers who talk like Howard Cosell.

Of course, I can’t forget the beautiful French foreign exchange student who catches John’s eye and utters a hilarious line about testicles.

And keep an eye on John’s little brother.

I know you’ve never seen it, so why not plan a double feature of this and The Sure Thing?  You’ll thank me later.

Honorable Mention: I’m sure there are those of you demanding to know why High Fidelity, Grosse Pointe Blank, Being John Malkovich, and Sixteen Candles did not make the list.  My answer would be that it’s because a Top 5 only has five slots!

What are your thoughts on my list, Modern Philosophers?  What’s your favorite John Cusack flick?  Will you promise to watch these now that I’ve given them my official Modern Philosopher seal of approval?

About Austin

Native New Yorker who's fled to the quiet life in Maine. I write movies, root for the Yankees, and shovel lots of snow.
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48 Responses to My Top 5 John Cusack Flicks

  1. NotAPunkRocker says:

    Grosse Point Blank, then 1408. 🙂

  2. 1wanderingtruthseeker says:

    Midnight in the Garden of good and evil.

  3. Son of Sharecroppers says:

    I’m a big fan of “The Grifters.”

  4. K. Renae P. says:

    Not gonna lie. He is one actor whose movies I consistently enjoy watching even though he is far from my favorite.

  5. Love High Fidelity – one of the only films where I prefer it to the book!

  6. Louise says:

    say anything I have not watched, but con air is my fav. b cos it has Nicholas cage in it also. grosse pointe blank is good, what about Must love dogs?

  7. Marneymae says:

    Grosse Point Blank.
    Then, Say Anything

  8. ksbeth says:

    love him. my favs are grosse point blank and better off dead. could watch each of them forever and never get tired of them )

  9. ofopinions says:

    1) High Fidelity 2) Say Anything 3) Better Off Dead + One Crazy Summer (same director, both crazy films!) 4) The Sure Thing 5) Grosse Pointe Blank. I didn’t like Hot Tub Time Machine, but liked 2012. Would you recommend War Inc.? I like both his Woody Allen films but not the ones he did with james spader and al pacino.

  10. D. Parker says:

    Say Anything, was good, but not his best, for me. The rest of your list is spot on, my favs of JC are: Tapeheads, PushingTin, Martian Child, Better off Dead, Being John Malkovich, Grosse Point Blank, Eight Men Out, Grace Is Gone, Sixteen Candles, 1408…oops, is that over 5, there are obviously too many amazing John Cusack movies. 🙂

  11. drishism says:

    Solid list! “Say Anything” is one of my favorite movies (not just among Cusack movies)

  12. Pingback: My Top 5 Letters Of The Alphabet | The Return of the Modern Philosopher

  13. markbialczak says:

    Yes for sure on “Say Anything” because Lloyd Dobler almost brought back boom boxes and single-footedly made kickboxing cool, you know, Austin? And “The Sure Thing” because co-star Daphne Zuniga made me look for Cassiopia. I’ll add to the list a late-comer, “Adult World,” in which our grown man Cusack plays a very cranky washed-up poet/prof who takes an impressionable student under his wing after much protestation. It was filmed in Syracuse. Rent it if you can.

  14. rozaliadame says:

    Reblogged this on The Uncanny Sublime and commented:
    Happy Birthday to Modern Philosopher!
    Here is one of my favourite posts by him… Because really, who doesn’t love John Cusack? -<3

  15. 1) High Fidelity. I will watch that constantly, it’s embarrassing at this point, but I love his record store. I love his apartment. I love his girlfriend. I just like the whole movie. It is basically the end of my high school and early college days in one place. 2) Grosse Pointe Blank…same deal. 3) Midnight in the Garden of Good and Evil. I liked his character. I also liked the way he walks… 4) Martian Child, and 5) 16 Candles.

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