Leading men of fall-set TV shows and movies

By Neia Balao 4:57am PDT, Sep 9, 2020

What better way to transition into fall than to take a look at our favorite leading men from film and television shows that take place during the autumn season? From Harry Burns in "When Harry Met Sally" to Luke Danes on "Gilmore Girls," Wonderwall.com is celebrating the leading men of fall-set movies and TV shows… starting with this Hollywood heartthrob. Before his days as Neo and John Wick, there was a time Keanu Reeves played the leading man in romantic dramas and comedies. In 2001's "Sweet November," Keanu took on Nelson Moss, a man who unexpectedly falls in love with Sara Deever (Charlize Theron), a woman he meets by happenstance at the DMV. Charming, selfless and incredibly smitten, Keanu plays Nelson to perfection. Keep reading for more…

In 1997, Matt Damon co-starred alongside Robin Williams in the drama "Good Will Hunting," which he co-wrote with Ben Affleck. In the flick, Matt played the titular role of Will Hunting, a 20-year-old genius and janitor at the Massachusetts Institute of Technology. As he begins to see a therapist, Dr. Sean Maguire (Robin Williams), he eventually begins to let his guard down and in turn begins to recognize his own potential. A brooding, self-taught genius in need of support and a push in the right direction? We can get behind that. A standout moment of the film: when Will leaves a note for Sean telling him he had to go "see about a girl."

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"When Harry Met Sally" is a classic romantic comedy that puts us in the perfect autumnal mood. As for its leading man? Harry Burns (Billy Crystal) is certainly among the most prominent characters in the romantic comedy genre. While he initially starts off as pessimistic bachelor unable to fathom the idea that men and women can be "just friends," we see him evolve into a stand-up guy with an altered perspective upon developing feelings for Sally (Meg Ryan). Harry's grand gesture at the end of the 1989 film — a moment for these two characters that was 12 years in the making — offers the clearest sign of his transition from cynical and jaded to a man capable of falling in love.

Texas, Forever! High school football season commences when fall rolls around, so it only makes sense to include one of our favourite fictional athletes on this list! Tim Riggins, played effortlessly by Taylor Kitsch, is the perfect manifestation of what a brooding, complicated teenage football star looks like. Tim is equally at odds with himself as he is with those around him — and this is made abundantly clear by the poor decisions he makes (i.e., hooking up with his recently disabled best friend's girlfriend and romancing his next door neighbor who is many years his senior). Still, even when he makes a slew of bad decisions, we can't help but root for him, because at his core, Tim is a well-intentioned guy. He's trying to figure life out as best he can and, as shown by his loyalty to older brother Billy (Derek Phillips) — for whom he literally goes to jail — the good in him always outweighs the bad. Tortured, pensive and oh-so-charming, Tim is a standout leading man in fall television.

It's common knowledge that the Pearson family patriarch on NBC's "This Is Us," Jack Pearson, is one of television's most upstanding characters. An example of this came in the 2016 season 1 episode "Pilgrim Rick" in which Jack does everything in his power to salvage what's left of his family's Thanksgiving after car trouble derails his initial plans to dine with love Rebecca's (Mandy Moore) mother. Instead, the family shacks up in a motel and celebrates the holiday amongst themselves. Time and time again, Jack manages to prove why he's one of television's most beloved dads. We miss you, Mr. Pearson.

Jack isn't the only Pearson man who gets a nod on our list! His adopted son, Randall Pearson — who's played by Golden Globe-winning actor Sterling K. Brown — is also an exemplary family man. Often seen pushing himself well past his limits, the "This Is Us" character never wants to let his loved ones down — which is seen in the way he takes care of mom Rebecca (Mandy Moore) and in how he takes precautions to protect wife Beth (Susan Kelechi Watson) and their girls (Lyric Ross, Eris Baker, Faithe Herman) after their home is broken into. Despite struggling with his own mental health, Randall works relentlessly to provide for those around him, even if it means putting his own needs aside to do so.

What makes John Keating such a memorable character is the way in which he inspired his students. Played to perfection in 1989's "Dead Poets Society" by Robin Williams — who earned a best actor Academy Award for his performance — his presence at Welton Academy was refreshing as his students, having gotten used to the insurmountable pressures of having to succeed academically, suddenly found themselves being taught by someone who encouraged their creativity and the notion of seizing the day. John, with of all of his passion, did for these boys what no teacher had ever done: Reinvigorate their sense of worth.

We couldn't cultivate a list of fall leading men without including this charming (albeit, incredibly aloof) high schooler. In 1994's short-lived coming-of-age series "My So-Called Life," Jared Leto delivered a breakout performance as Jared Catalano, the object of Angela Chase's (Claire Danes) affection. What makes Jordan such an intriguing character is the fact that he, in a way, turns the stereotype of an inarticulate bad boy on its head. Throughout the series — which takes place almost exclusively in the fall months — we see him struggle to convey his emotions (like when he enlists fellow student Brian's help to literally write a love letter to Angela), not because he's unable to but because his own lack of confidence gets in the way. Jordan, with all of his airy delight, is more complex than he's often given credit for.

The 2000 movie "Autumn in New York" stars Richard Gere as Will Keane, a successful 48-year-old restaurateur who initially has no intention of settling down or changing his womanizing ways. However, his entire perspective on life is changed upon meeting Charlotte Fielding (Winona Ryder), a 22-year-old woman with a tragic secret with whom he develops a connection. From self-serving to falling in love, Will evolves drastically over the course of the film.

In Nora Ephron's classic 1998 romantic comedy "You've Got Mail," Tom Hanks stars as Joe Fox, a member of the affluent Fox family that owns a chain of popular bookstores. When he finally learns that he's actually been corresponding romantically with his business rival, independent bookstore owner Kathleen Kelly (Meg Ryan), Joe is forced to decide whether or not he's willing to set aside their differences in order to pursue a real-life relationship with her — and, thankfully, he does! From corporate and competitive to recognizing his true feelings for Kathleen, Joe is one of our favorite leading men on this list!

Tim Burton's classic 1993 holiday tale "The Nightmare Before Christmas" follows Jack Skellington, the "Pumpkin King" of Halloween Town. A genuine, upstanding member of the undead, Jack has always taken measures to ensure that everything he does is in the interest of the townspeople. Perhaps his most commendable trait is his ability to recognize his faults and when it's time to relinquish control. When he realizes he's ruined Christmas, Jack admits his wrongdoings and goes to Santa Claus for help. By setting his pride aside and coming to terms with the fact that he may be naive at times, Jack proves himself to be a good-hearted leader.

Contrary to popular belief, not every high school football player is a huge fan of the sport! In 1999's "Varsity Blues," Jonathan "Mox" Moxon (James Van Der Beek) exemplifies this perfectly. A smart, academically inclined student at West Canaan High School, Mox has big plans for his life — which include attending prestigious Brown University. This plan, of course, is thrown into question when he's called up as the team's starting quarterback after star athlete Lance Harbor (Paul Walker) suffers a knee injury. Through Mox, we witness a teen who is forced to shoulder the dreams of team he doesn't have much interest in being a part of.

We first meet FBI Agent Dale Cooper (Kyle MacLachlan) in the 1990 "Twin Peaks" pilot when he comes to town to investigate the mysterious murder of troubled teen Laura Palmer (Sheryl Lee). Exceptionally polite without even a hint of an ulterior motive, Dale is a glowing example of what it means to be a good man who is good at his job. Dale — a detective who remains optimistic in the face of incredible danger (and has a penchant for coffee) — is not only a standout leading man but a standout fictional character in general.

Serious question: Is there any show that serves more fall vibes than "Gilmore Girls"? As early as the 2000 pilot, we start to get to know Luke Danes (Scott Patterson), the proud owner of the town's beloved hotspot Luke's Diner. There's something about Luke — who's consistently dressed in an oversized flannel and a backwards cap — that screams autumn. Having a hot cup of coffee at Luke's Diner, while being surrounded by the orange and yellow hues of fallen leaves in Stars Hollow, Connecticut? Talk about a dream scenario.

Another series that kicks off in the fall? "The Vampire Diaries." While fans remain divided on whether or not they are on Team Stefan or Team Damon, Stefan (Paul Wesley) was the first Salvatore brother to capture our hearts. We first met Stefan and all of his brooding glory in 2009 when he mysteriously enrolled at Mystic Falls high school and ran into Elena Gilbert (Nina Dobrev). It wasn't long until we watched their fiery "teen" romance unfold during the first few months of the school year. Mystic Falls, a historic town steeped in an ominous supernatural past, makes for the perfect, perpetually autumnal setting for this moody series.

When we first met "Teen Wolf" star Scott McCall (Tyler Posey) in 2011, he was initially an unpopular high schooler without any athletic prowess. However, upon being bit by former Alpha Peter Hale, his entire life changes drastically — suddenly, Scott finds himself gifted with superhuman strength, speed and healing abilities. As the series progresses, especially in the first season, we see Scott acclimate to his new Beta werewolf self as well as navigate the complexities of adolescence and sophomore year.

What's not to love about Noah Centineo's portrayal of Peter Kavinsky in "To All the Boys I've Loved Before"? Charismatic, handsome and wildly charming, it makes sense why Lara Jean Covey has such a hard time not catching feelings for him! Since the film starts at the beginning of the school year, we watch Peter and LJ's fake relationship progress throughout autumn and deepen in the process. From attending high school parties together to that infamous moment on the senior ski trip, Peter proved he's truly the fall leading man of our dreams!

In the Academy Award-winning film "Silver Linings Playbook," Bradley Cooper stars as Pat Solitano, a man who's recently completed eight months of treatment at a mental health facility in Pennsylvania. Over the course of the film, which came out in 2012, we see Pat drastically change — he goes from a man obsessed with reconciling with his ex-wife (Brea Bee) to one who's actually proud of who he's become. Instead of remaining stagnant and pining after the woman he lost, he develops a close bond with Tiffany Maxwell (Jennifer Lawrence), a misunderstood woman with borderline personality disorder. Upon agreeing to partner with Tiffany for a dance competition, Pat slowly but surely begins to realize his feelings for her, which culminate in an epic, poignant declaration of love after they earn an average score of 5.0 at the competition.

Jake Gyllenhaal stars as Homer Hickam, a young rocket science enthusiast in 1999's "October Sky." The film kicks off in October 1957 following the launch of the Soviet Union's Sputnik 1. Enthralled by the sight of the satellite over his town of Coalwood, West Virginia, Homer grows inspired to build his own rockets in an effort to escape to a better life — a life outside of coal mining. Intelligent, aspirational and filled with wonder, Homer exemplifies what it means to chase after your dreams in spite of people who try to take them away from you.

The "Chilling Adventures of Sabrina," which debuted on Netflix in 2018, found its Harvey Kinkle in actor Ross Lynch. As far as high school sweethearts go, Harvey was a glowing example of what a stellar boyfriend should be like: His close connection with Sabrina was apparent from the get-go and their relationship was strengthened by their support and care for one another. Harvey — the son of a coal miner and descendant of witch hunters — uses his unique ability to aid Sabrina in the fight against the dark forces that continue to wreak havoc around them. Charming, supportive and well-meaning, Harvey made for a refreshing addition to the spooky town of Greendale.