I’m not sure if it’s in spite or because of the wildly varied career that he has had, but it feels hard to overstate how beloved John Cusack is to a certain segment of the moviegoing population. In recent years he’s appeared in a number of thrillers and genre films that haven’t received as much attention as his earlier work, but Cusack’s palpable intelligence and unforced charisma on screen were absolutely iconic in a spate of 1980s and ‘90s teen comedies and coming of age stories  where he either played the guy that you wanted to be with, or simply the guy you wanted to be. As we commemorate the gifted and charming actor’s 53rd birthday on June 28, Moviefone takes a look back at just a few of the films that made us fall in love with John Cusack.

“The Sure Thing” (1985)

After small but memorable roles in “Class” and “Sixteen Candles,” Cusack got his first big role in Rob Reiner’s follow-up to “This Is Spinal Tap,” a romantic comedy about two bickering college students (Cusack and Daphne Zuniga) who make a cross-country trip to meet their perfect partner, only to discover that the one they’re looking for is right in front of them.

“Better Off Dead” (1985)

A decidedly goofier look at teenage romance than “The Sure Thing,” Savage Steve Holland’s story about high schooler Lane Myer (Cusack), his best friend Charles De Mar (Curtis Armstrong) and the girl (Amanda Wyss) that broke his heart  remains one of the most madcap and irresistible comedies of the 1980s. Plus, Diane Franklin of “Last American Virgin” fame plays Monique, the French exchange student who deservedly wins his heart.

“Eight Men Out” (1988)

John Sayles was a powerhouse storyteller in the 1980s, and in this recount of MLB’s 1919 Black Sox scandal, Cusack plays Buck Weaver, a shortstop whose career ended in disgrace after taking the fall for his teammates when they attempted to throw the World Series. Cusack’s quiet resolve -- but also his solidarity in not revealing the fix -- provides a perfect counterbalance to the tragic consequences of this stain on Major League baseball’s history.

“Say Anything…” (1989)

Few characters have ever been as universally beloved as Cusack’s Lloyd Dobler, the kickboxing-loving high school graduate who falls for valedictorian Diane Cort (Ione Skye) in Cameron Crowe’s unforgettable directorial debut. The two them make an adorably awkward pair as their love finds footing against the backdrop of his aimless future and her escalating family troubles. Plus that boombox scene is just iconic.

“The Grifters” (1990)

Cusack is both the genius and the fool in Stephen Frears’ adaptation of the Jim Thompson novel of the same name. Playing Roy Dillon, the estranged son of veteran con artist Lily (Anjelica Huston), Cusack gets to exercise his oiliest charms as well as his stone-faced gullibility when they make a tenuous pact with his girlfriend Myra (Annette Bening) for a long con that tests loyalties and promises deadly consequences.

“Grosse Pointe Blank” (1997)

Cuscak co-wrote this comedy, directed by George Armitage, about a hitman who comes home for his ten-year high school reunion. Revisiting the choices of his past -- the biggest being the abandonment of his girlfriend Debi (Minnie Driver) on prom night -- Martin Blank goes on an explosively fun journey that ends when he discovers either that he’s still in love with Debi or he develops a newfound respect for life.

“The Thin Red Line” (1998)

The number of people whose roles Terrence Malick cut down or completely out of this James Jones adaptation are reportedly legendary, but even in a small part of this operatic, meditative war film, Cusack leaves a very distinct impression as an army captain whose quiet authority prompts his ambitious, volatile superior officer (Nick Nolte) to reward his men after they mount a successful attack on a bunker at the cost of dozens of lives.

“High Fidelity” (2000)

Cusack’s second outing as a co-writer created a decidedly less flattering portrait of love and relationships, but this adaptation of the Nick Hornby’s novel remains a seminal work in his filmography. His Rob Gordon serves as an iconic and transformative character after what was previously a mostly uninterrupted spate of nice guys and charmers.

“Serendipity” (2001)

Cusack retreated to the familiar territory of rom-coms to play another irresistible leading man for this inventive film about two people (Cusack and Kate Beckinsale) whose fates become intertwined after they attempt to purchase the same pair of cashmere gloves for the partners they don’t know yet are just an obstacle to finding each other.

“Hot Tub Time Machine” (2010)

Cusack’s longtime pal Steve Pink directed this trip down memory lane for the onetime ‘80s heartthrob playing a down-on-his-luck guy who gets magically transported back to his youth to fix some of the mistakes that led to his unhappy adulthood.

“Love & Mercy” (2014)

Beach Boys co-founder Brian Wilson had such a fascinating life that not one but two people had to play him in this unconventional biopic. As the middle-aged Wilson, coddled into inactivity by a manipulative therapist, Cusack provides compelling layers of charm and humanity that elevate a performance that could easily have been doddering and aloof.