To me, there are fewer more iconic film roles from my lifetime than John Cusack‘s Lloyd Dobler in Cameron Crowe‘s fantastic tale of late 80’s high school love Say Anything. While his role as Lane Meyer in Better Off Dead will always be my favorite of his, Cusack‘s portrayal of Dobler is what earned him his most acclaim as an actor up the point of Say Anything‘s release and launched him as a bona fide leading man. Cusack is somewhat of a Hollywood enigma, almost known more for turning down famous roles than for the eclectic roles he has chosen. For example, he turned down Bill Paxton‘s role in Apollo 13, Woody Harrelson‘s role in Indecent Proposal, Greg Kinnear‘s role in As Good As it Gets, and most recently, the role of Walter White in the TV scorcher Breaking Bad (among many others). Few have seen his turns in cult classics like the bizarre, yet oh-so-wonderful Tapeheads (one of my all-time faves) or Hellcab. But Lloyd Dobler people have seen and really connected with.

Lloyd is the son of a Lt. Col in the Army. He lives with his sister (played by real life sister and frequent collaborator, Joan Cusack) and her son while he finished out high school in Seattle. On the cusp of graduation, he, a man whose interests are loud music and kickboxing, decides to ask out Diane Court (Ione Skye), his school’s valedictorian and a girl he has convinced himself that he had a first date with already (they ate across from one another at a mall). When she decides to go with him to the annual graduation bash held at the same guy’s house (an almost unrecognizable Eric Stoltz), he has pulled off a major coup. When asked how this “happened”, Diane says,”He made me laugh.” See boys, every girl, even smart ones who are hot love a sense of humor.

The two hit it off and Lloyd makes it his task to be with Diane as much as a he can before she leaves for England on a prestigious fellowship. This, of course, rubs her father (John Mahoney) the wrong way as he wants her thoughts to be on the fellowship and accomplishing what she has set out to do with her life since she was 5 – BE GREAT. Lloyd, to him, is just a distraction.

When Mr. Court finds out he is under investigation by the IRS for tax fraud, her attention is clearly not on her studies and fellowship, so Lloyd provides much needed distraction from her problems at home. Of course the two have sex and it christens their relationship. Even Lloyd’s best friends, Cory (Lily Taylor) and D.C. (Amy Brooks), believe they are destined for greatness. Since Diane and her father are so close, she tells him everything and she lets him know they slept together. But sneaky as he is, he finds a way to get them to break up, which devastates Lloyd who, in turn, goes searching for answers. Figuring he needs to spend more time with guys, he finds them…at the Gas & Sip:

He clearly doesn’t find what he’s looking for and flips out leading to perhaps the funniest part of the whole film:

“Lloyd, Lloyd, all null and void…” – is there a better opening to a rap song ever (well, besides Wu Tang‘s “Triumph”)? Lloyd struggles to understand why she cut him loose…and left him with only a pen.

Despite his best efforts to keep from doing so, he pursues Diane in an attempt to win her back. Without a doubt, this pursuit created the most iconic image and scene of the film – Peter Gabriel‘s “In Your Eyes” and a boombox at dawn. You know what I’m talking about – it’s been aped and repurposed a million times over by now. Damn it. Cusack and Crowe, you bastards. Not only did you create arguably the most romantic scene of 80s high school films, but you set expectations of women for the next one hundred years so high that no one man possibly reach them. Every Jane, Amy and Jenny now expect grand gestures such as these when, at no fault of our own, men wish to win our loves back after some hasty break-up caused by the girls’ shifty, criminal fathers. Shame on you. Get on the same team.

Couple this with Cusack‘s subsequent role in 2000’s High Fidelity where Rob Gordon, via Nick Hornby‘s novel and Cusack and friends who wrote the script, allows women behind the curtain of the male psyche giving away nearly all of our secrets. You’re killing me, Johnny.

All that aside, Say Anything is one of the few films I ever watched with my grandma because it has that broad of an appeal. And she loved it. I could break down how it all plays out, but that shorts you from watching it for the first time or revisiting it, which is still a treat. Cusack made the leap from goofball king from his time in the Savage Steve Holland films Better Off Dead and One Crazy Summer to bona fide beau hunk in one film. He seemed to come back from time to time to tap this well over the course of his career (which has all but ended to me with High Fidelity), he had chosen more obscure fare for the most part (Being John Malkovich, anyone?). Now, it just seems like he’s drawing a paycheck. Like I said, your all-American boy.

Nevertheless, Say Anything remains one of the more cherished films, for it’s sentiment more than anything, of my high school/teen years. You would do well to watch it. Cusack demonstrates why he was once one of the more sought after young actors in the biz. Fair play to you, John.

Here’s the trailer: