My Favourite Tobey Maguire Movies of All-Time

10 Best Tobey Maguire Movies, According to IMDb
Best Tobey Maguire Roles That Aren't Spider-Man

Not many actors in Hollywood have made movies audiences admire like Tobey Maguire. Since the 1990’s, Maguire has become an icon. Whether it’s web-swinging teens, alcoholic swingers or traumatized soldiers, Maguire has played several strong characters. Given the number of movies he has made, making a top 10 list isn’t easy. Nevertheless, listed below are my picks for the best movies of an actor that deserves to be celebrated.

1. Spider-Man 2

Spider-Man is a spectacular superhero that shaped my teacher’s identity. Several years ago, I formed strong bonds with a teacher that appreciated the web-swinging superhero. A comic-book nerd, he spoke fondly about a superhero making him feel heard. He would always praise a legendary hero whose great powers came with great responsibilities impacting his identity. His classroom was always decorated with posters of a superhero that he appreciated. Through his words of wisdom, I was motivated to pursue a career in film criticism. As someone treasuring memories of a teacher that grew up to value Spider-Man, I adored “Spider-Man 2”. Ever since its release in 2004, Tobey Maguire’s movie has stood the test of time as a comic-book classic. In the greatest role of his career, Maguire embodies a conflicted superhero struggling to spin webs in the air facing despair. This is the actor unlike you’ve ever seen him before: intense, charismatic and emotional in his most iconic role. Maguire has always had an aptitude for playing Spider-Man throughout cinematic history. With “Spider-Man 2”, however, the actor showcased emotional vulnerability he hadn’t shown as the character before. For instance, the scene in which Spider-Man is frustrated to find that he has lost his powers being unable to swing webs in the air is one of the best moments of the actor’s career. Ultimately, what makes “Spider-Man 2” a classic is its humanity. Unlike most comic-book movies, it tackles universal themes that everyone would relate to. It manages to turn Spider-Man into an ordinary hero with flaws whom anyone can relate to. Nearly 20 years following the release of a comic-book film about a superhero whose great powers come with great responsibilities that are challenging, it’s a breathtaking reminder of a commemorated actor whose movies are worth celebrating.

THE GREAT GATSBY Review ~ Reviews From A Bed

2. The Great Gatsby

The Great Gatsby is a great book that my cousin has always loved dearly.  Ever since it was published in the 1920’s, The Great Gatsby is a book that my cousin has cherished. An avid reader, he would always speak fondly about a piece of literature he grew up to treasure. As someone treasuring fond memories of a cousin that loved a book about millionaires shaping his identity, I adored “The Great Gatsby”. Released in 2013, Tobey Maguire’s movie celebrated classic literature. In the most thoughtful role of his career, Maguire embodies a conflicted writer that becomes enamoured by his neighbour millionaire carrying a heavy burden to bear. Maguire is one of those actors that has always thrived at using voice-over narration to convey emotion, and “The Great Gatsby” showcased his strengths as a vocal performer. Working alongside Leonardo DiCaprio who is also excellent, Maguire honoured a legendary book written years ago. For instance, the scene in which Nick Carraway expresses astonishment when he finally meets the mysterious Gatsby at his party is one of the most memorable moments of the actor’s career. Ultimately, what makes “The Great Gatsby” a great adaptation is its meaningful message. The film delivers a profound message about social class resonating with everyone. A century following the publication of a great book about millionaires whose dreams deteriorate, it’s a strong reminder of an actor whose movies audiences appreciate.

3. Spider-Man

It’s challenging to face the loss of a loved one. Several years ago, my family experienced grief when our uncle passed away without relief. As wise as Uncle Ben, he was a person that my family had grown to idolize. His heartbreaking passing left my family mourning. Loss is a common theme explored throughout the Spider-Man franchise. However, it is arguably most evident in the first Spider-Man movie. Released in 2002, Tobey Maguire’s first Spider-Man movie honoured the web-swinging superhero through exploring themes of loss. In the most emotional role of his career, Maguire embodies a conflicted superhero facing the loss of an uncle causing despair. Maguire is one of those actors that has always excelled at showcasing emotions through his expressions, and his strengths are evident in “Spider-Man”. For instance, the car scene in which Peter Parker experiences a heartwarming conversation with his uncle about his great powers that come with great responsibilities showcased the actor at his best. Ultimately, what makes “Spider-Man” a comic-book classic is its message. The film delivers a meaningful message about loss that will resonate with everyone. As spectacular tribute towards a web-swinging superhero whose great powers come with great responsibility, it’s a strong reminder of an actor whose movies audiences love dearly.

4. Babylon

Drug addiction is a serious issue that affects celebrities in Hollywood. During my childhood, I formed a friendship with a kid addicted to drugs. His addiction to weed put him on a path to fail rather than succeed. Nevertheless, I got along well with a student fascinated by drugs casting a magical spell. As someone treasuring fond memories of a companion with drug addiction, I loved “Babylon”. Released in 2022, Tobey Maguire’s movie offered a dazzling depiction of drug addiction impacting celebrities in 1920’s Hollywood. In the most psychotic role of his career, Maguire embodies an eccentric gangster that suffers from severe drug addiction that’s a burden to bear. With “Babylon”, the actor took a step out of his comfort zone by playing a detestable drug addict. For instance, the scene in which McKay is first introduced taking Manny to a depraved sex club showcased the actor at his best. Ultimately, what makes “Babylon” a masterpiece is its message. The film delivers a meaningful message about drug addiction which would resonate with everyone. A dazzling depiction of drug addiction that impacts celebrities lacking life direction, it’s a dazzling reminder about an actor whose unforgettable movies are deserving of celebration.

5. Brothers

As far as I can remember, I’ve always shared a strong bond with my brother. During my childhood, my brother loved playing the game of soccer in our neighbourhood. Born with a strong physique of a warrior, my brother enjoyed playing soccer every week. After he left for university, I sorely missed a brother that shaped my identity. As someone treasuring heartwarming memories of brothers, I adored “Brothers”. Released in 2009, Tobey Maguire’s movie captured the life of a war veteran with PTSD facing a broken relationship with his brother. In the most emotional role of his career, Maguire embodied a war veteran enduring broken relationships with his brother facing despair. It’s a tough role far removed from Spider-Man that gave the actor an opportunity to step out of his comfort zone. For instance, the scene in which Sam confronts his wife about cheating on him is one of the greatest moments of the actor’s career. Ultimately, what makes “Brothers” a masterpiece is its message. The film delivers a powerful message about bonds between brothers which would resonate with everyone. A powerful portrait of bonds between brothers that decline, it’s a strong reminder of an actor that has made memorable movies which shine.

6. The Cider House Rules

When it comes to the greatest books ever written about rules, it’s worth discussing “The Cider House Rules”. Since its publication in 1985, John Irving’s book has stood the test of time as a literary classic. In 1999, Tobey Maguire did an extraordinary job adapting the beloved book about house rules in his film “The Cider House Rules”. In the most innocent role of his career, Maguire embodied a sweet-natured orphan that faces despair. It’s a compassionate role that gave the actor an opportunity to showcase his aptitude for playing innocent characters. Working alongside Michael Caine who is also excellent, Maguire honoured a commemorated book readers admire. A beautiful adaptation of a beloved book about house rules, it’s a strong reminder of a commemorated actor whose memorable movies audiences regard as jewels.

Viewer Guide: Pleasantville and Carol | Blog | Reel 13 | THIRTEEN

7. Pleasantville

One of the most common criticisms levelled against Tobey Maguire is that he doesn’t take risks as an actor. Since his career began years ago, Maguire has been typecast as a superhero. Maguire’s association with Spider-Man has left little room for surprises in the actor’s career. However, in 1998 Maguire took audiences by surprise proving he hadn’t lost his abilities to thrill when he made his film “Pleasantville”. In the most unusual role of his career, Maguire embodies a sibling facing confusion when he becomes trapped in a black-and-white television show on air. It’s an out-of-the-ordinary role that gave the actor a chance to step out of his comfort zone playing a character far removed from Spider-Man. As precious as the town of Pleasantville, it’s a powerful reminder of an actor that hasn’t lost abilities to make movies that thrill.

Seabiscuit (2003)

8. Seabiscuit

When it comes to the most beloved racehorses in American history, it’s worth discussing Seabiscuit. During the 1940’s, Seabiscuit was a celebrated racehorse that achieved awe-inspiring victories. A horse with stamina that was inspiring, Seabiscuit built a legacy which was lasting. In 2003, Tobey Maguire did an extraordinary job telling the true story of the racehorse in his film “Seabiscuit”. In the most athletic role of his career, Maguire embodies a horse-rider facing a burden to bear. It’s a role that gave the actor an opportunity to showcase his aptitude for playing athletic characters. Working alongside Jeff Bridges who is also excellent, Maguire honoured a racehorse. Nearly 90 years after Seabiscuit became a legendary horse that would conquer every race, it’s a riveting reminder of an actor whose timeless films audiences embrace.

9. Wonder Boys

Teachers are inspiring figures that shaped my identity. I remember an English teacher that gave me goals to accomplish. His inspiring words of wisdom motivated me to pursue dreams of film criticism. As someone treasuring fond memories of a wonderful teacher that loved educating boys, I adored “Wonder Boys”. Released in 2000, Tobey Maguire’s movie offered an insightful depiction of teachers shaping students’ identities. In the most provocative role of his career, Maguire embodies a gay student that engages in a romantic affair with a teacher that’s a burden to bear. It’s a risky role that gave the actor a chance to showcase his strengths beyond being Spider-Man. A touching tribute towards teachers that inspire wonder, it’s a terrific reminder of a tremendous actor whose commemorated movies audiences treasure.

How Spider-Man 3 was derailed by Venom and studio interference

10. Spider-Man 3

Tobey Maguire hasn’t always made movies that audiences admire. While most movies the actor has made have turned out successful, others have fallen short. Unfortunately, “Spider-Man 3” falls into the latter category of movies that failed terribly. Released in 2007, Sam Raimi’s blockbuster was a disaster that fell short. In the most wooden role of his career, Maguire embodies a hero that faces despair. Maguire brought charisma to Spider-Man proving to be the bright spot of an otherwise bad movie. Despite being a flawed movie, “Spider-Man 3” remains a worthy reminder of Maguire’s legacy. As strong as Spider-Man’s desire to defeat Venom, it’s a strong reminder of an actor that has achieved stardom portraying characters with heroism whose memorable movies I will forever treasure for inspiring me to pursue dreams of film criticism.