Soundtracking is a regular column that appears on Cineplex.com looking at the music featured in the biggest new releases both in theatre and on home video. Shane McNeil looks at the lovesick musical ouevre of John Cusack .

Originally published on Cineplex.com – February 10, 2014.

Valentine’s Day is nearly here and what better way to celebrate than with a look at the man every girl wants to be their boyfriend: John Cusack.

Ever since he declared “I want to get hurt!” in the opening scene of Say Anything… Cusack has embodied the ideal in vulnerability and awkward sweetness to most females of a certain age.  And since the mixtape has been scientifically proven to be the highest expression of love from one human being to another, here – for all of you – is a Valentine’s mixtape from John Cusack.

Cusack stole a generation’s heart as Lloyd Dobler in Say Anything… in 1989, a sweet loser that bets it all on the girl of his dreams and wins her over by just being a good guy.

Under the direction of Cameron Crowe, Dobler’s pursuit of Diane Court (Ione Skye) takes us through the likes of Aerosmith and Depeche Mode before Dobler’s passionate plea for understanding with Peter Gabriel.

The secret to Cusack’s appeal has been that he’s such a believable everyman that he has built an entire career on always being able to bring a dash of Dobbler both on- and off-screen. As noted pop culture critic Chuck Klosterman put it: people “assume when the camera stopped rolling, he went back to his genuine self…which was someone like Lloyd Dobler.”

So, when Cusack played hit man Martin Blank eight years later, it was Dobbler coming back for his high school reunion. But, of course, the soundtrack of his life had not changed.

The 1980s have rarely had it so good (since, say, the 1980s) as they did on the Grosse Pointe Blank soundtrack.  Trying to win the heart of local DJ Debi Newberry, Blank uses her own weapon – the music – as a means for nostalgic advancement.  From the opening strains of Johnny Nash prior to the opening credits, the music of Grosse Pointe is a force greater than even Say Anything.

We go through Debi’s DJ stand-bys such as The Violent Femmes and The Clash before the big moment at the reunion. Martin and Debi finally get their reconciliation moment – albeit briefly – under the strains of Pete Townshend’s “Let My Love Open the Door”.

But things don’t always go to plan for Cusack and three years after Grosse Pointe we saw him melt down in High Fidelity.

If Dobbler was Cusack for the ladies, then High Fidelity‘s Rob Gordon is Cusack for the fellas: A brooding, slightly petulant record obsessive who’s seemingly been on the losing end of every relationship.

This fact comes out through the shelves of vinyl that threaten to collapse and fill his apartment at seemingly any moment. Gordon’s misery is refracted through the lens of 13th Floor Elevators, Bruce Springsteen, and The Velvet Underground.

He does, of course, come around eventually and the film’s final few scenes are a soul-filled victory lap to the likes of Marvin Gaye and Stevie Wonder, but the final statement on Cusack’s career in romantic torment  – the final song on his mix tape, if you will – has to be an uplifting one.

Who knows Valentine’s Day like Jackie Wilson? Okay, maybe Sam Cooke … but still, Jackie Wilson!