Not many actors in Hollywood have earned recognition of Sean Penn. Since the 1990’s, Penn has become a beloved icon. whether it’s political leaders, death row prisoners or grieving fathers, Penn has portrayed many strong characters. Given the sheer number of movies he has made, making a top 10 list isn’t easy. Nevertheless, listed below are my favourite films made by a commemorated actor that deserves to be celebrated.
1. Milk
Harvey Milk is a legendary American politician that my cousin always loved dearly. Years ago, I witnessed a gay cousin seeking acceptance in Toronto. My cousin always admired Harvey Milk for the efforts he made changing rights for LGBTQ communities. He would always love discussing a gay activist that forever changed ways that LGBTQ communities are seen today. My cousin yearned to see the life of a legendary politician depicted on the big-screen. In 2008, Sean Penn honoured Harvey Milk in his movie “Milk”. In the greatest role of his career, the actor portrayed a legendary queer politician that carried a heavy burden to bear. This is the actor unlike you’ve ever seen him before: intense, charismatic and emotional in his most memorable role. Penn has spent most of his career playing fictional heroes in dramas. With “Milk”, however, the actor took a huge step out of his comfort zone by a legendary American politician that’s well-known. Working alongside Josh Brolin who is also outstanding, Penn honoured a politician that’s inspiring. For instance, the scene in which Harvey Milk delivers a rousing speech to the queer community seeking to prepare it for warfare is one of the finest moments of the actor’s career. Ultimately, what makes “Milk” Sean Penn’s best movie is its commemorated message. The film delivers a profound message about sexual identity which would resonate with everyone. Nearly 20 years following the release of a groundbreaking film about a celebrated gay activist that changed the way homosexual communities are treated experiencing a painful price to pay, it’s a breathtaking reminder concerning a commemorated actor that has manufactured unforgettable movies throughout his career which deserve to be appreciated today.
2. Mystic River
It’s challenging to come to terms with loss of a loved one. Several years ago, my family’s life hit crushing lows when our great housekeeper was killed causing sorrow. Stabbed to death in shower, my housekeeper became a victim of murder. No matter how hard my family tried, we couldn’t recover from loss of a housemaid that died. As someone haunted by the death of a beloved housekeeper, I adored “Mystic River”. Released in 2003, Sean Penn’s movie offered an engaging murder mystery. In the most emotional role of his career, Penn portrayed a grieving father seeking to cope with murder of his daughter causing despair. It’s a role that gave the actor a chance to showcase his talent for playing emotional heroes under intense pressure. Working alongside Kevin Bacon who is also amazing, Penn created a murder mystery that’s captivating. For instance, the scene in which Jimmy first becomes aware that his daughter has been murdered causing despair is one of the finest moments of the actor’s career. Ultimately, what makes “Mystic River” a classic is its message. The film delivers a bold message about loss which will resonate with everyone. A breathtaking portrait of frightening murders causing the lives of men to deteriorate, it’s a bold reminder of a great actor making memorable movies in his career which audiences commonly appreciate.
3. Licorice Pizza
L.A. is a beautiful city that my father always loved dearly. During my childhood, I bonded with a father that was a huge fan of Hollywood. He would always marvel at the way that actors prepared for big roles in L.A. My father often yearned to see the city he loved dearly depicted on the big-screen. In 2021, Sean Penn honoured the iconic city in America with nostalgia in his movie “Licorice Pizza”. In the most authoritative role of his career, Penn portrayed a famous actor seeking success in a town facing despair. It’s a personal role that gave the actor a chance to draw from his own personal experiences as a movie-star in Hollywood. Working alongside Alana Haim who is also outstanding, Penn created a portrait of Los Angeles that’s compelling. For instance, the scene in which Jack Holden seeks to prepare for his first film shoot is one of the finest moments of the actor’s career. Ultimately, what makes “Licorice Pizza” a masterpiece is its universal appeal. Unlike most movies that are set in the city of Los Angeles, it tackles commemorated themes that everyone would relate to. It delivers a meaningful message about adolescence which would resonate with everyone. A touching tribute towards a forgotten era in Hollywood, it’s a breathtaking reminder of a commemorated actor that has stood test of time by manufacturing memorable movies that are good.
4. Dead Man Walking
Wrongful conviction has shaped my personality. During my childhood, my life changed when I was wrongfully accused of cheating on a science-fair project. Throwing a tantrum, a girl in my class accused me of plagiarism. As someone that witnessed wrongful conviction that’s frightening, I adored “Dead Man Walking”. Released in 1995, Sean Penn’s movie captured prisoners facing wrongful conviction. In the most conflicted role of his career, Penn portrayed a death row prisoner that faces wrongful conviction for a crime he hasn’t committed causing despair. It’s a role that gave the actor a chance to showcase his talent for playing emotional characters under intense pressure. Working alongside Susan Sarandon who is also amazing, Penn created a portrait of wrongful conviction that’s compelling. For instance, the scene in which Matthew becomes aware that he has been sentenced to death causing despair is one of the finest moments of the actor’s career. Ultimately, what makes “Dead Man Walking” a masterpiece is its universal appeal. Unlike most prison dramas, it tackles strong themes that everyone would relate to. The film delivers a message about wrongful conviction affecting everyone. A powerful portrait of the death penalty causing prisoners to crumble, it’s a bold reminder of an actor making unforgettable movies audiences consider special.
5. Into the Wild
Wilderness survivors experiencing grave danger always inspired my grandfather. I remember forming relationships with a grandfather appreciating wilderness survivors facing danger. Drawn towards the wild, he always loved discussing people surviving in wilderness leaving him beguiled. As someone treasuring memories of a grandfather that sought to journey into the wild, I admired “Into the Wild”. Released in 2007, Sean Penn’s movie honoured the true story of a wilderness survivor. Penn showcased skills behind the camera making his fist ever movie about wilderness causing trauma. For instance, the scene in which Christopher becomes aware of the dangers associated with the wilderness causing despair is one of the finest moments of the filmmaker’s career. Ultimately, what makes “Into the Wild” a masterpiece is its universal appeal. Unlike most movies about the wilderness, it tackles strong themes that everyone would relate to. It delivers a meaningful message about survival which would resonate with everyone. A wonderful tribute towards a man that survived in the wild, it’s a stirring reminder of a commemorated actor that has manufactured great movies throughout his carer leaving audiences frequently beguiled.
6. 21 Grams
Sean Penn has often excelled at playing emotional characters facing tension. Penn has built an image of being an actor that thrives at playing emotional heroes facing damage. Penn’s strengths for playing emotional heroes carrying grams is clearly evident in his movie “21 Grams”. Released in 2003, Alejandro Gonzalez Inarritu’s movie showcased the actor at his best. In the most complex role of his career, Penn portrayed a terminally ill man involved in an accident causing despair. It’s a role that gave the actor a rare chance to showcase emotional range he hadn’t shown before in his career. Working alongside Naomi Watts who is also amazing, Penn created a drama that’s engaging. A powerful portrait of a hit-and-run accident, it’s a riveting reminder of a celebrated actor with commitment that has always produced memorable entertainment.
7. The Thin Red Line
Over the past decade, the war movie genre has declined in quality. With their over-the top action, lacklustre storytelling and poor acting, most war movies have become a chore to sit through. In a genre that has lost its abilities to shine, it’s worth praising “The Thin Red Line”. Released in 1998, Sean Penn’s movie offered a powerful portrait of war tragedy. In the most heroic role of his career, Penn portrayed a brave soldier participating in warfare causing despair. It’s a role that gave the actor a chance to showcase his talent for playing emotional heroes under pressure. Working alongside Adrien Brody who is also outstanding, Penn created a war movie that’s captivating. As strong as Welsh’s desire to become a successful soldier, it’s a riveting reminder of a commemorated actor that has manufactured movies which audiences treasure.
8. I Am Sam
Intellectual disabilities are rarely depicted with respect in movies. Hollywood has often shied away from depicting complex mental disorders that are misunderstood. In an industry where intellectual disability is rarely given attention, it’s worth praising “I Am Sam”. Released in 2001, Sean Penn’s movie offered a powerful portrait of intellectual disability. In the most challenging role of his career, Penn portrayed an intellectually disabled father facing despair. It’s a sensitive role that gave the actor a chance to step out of his comfort zone by playing a disabled character. Working alongside Dakota Fanning who is also amazing, Penn created a portrait of disabilities that’s captivating. A portrait of disability causing lives of fathers to face trauma, it’s a riveting reminder of an actor with charisma making movies always attracting audiences towards Cinema.
9. Carlito’s Way
When it comes to the greatest books ever written about gangsters facing a price to pay, it’s worth discussing Carlito’s Way. Since its publication in 1975, Edwin Torres’ book has become a literary classic. In 1993, Sean Penn honoured the book about the way gangsters behave in his movie “Carlito’s Way”. In the most villainous role of his career, Penn portrayed a drug-addicted lawyer seeking to destroy the life of a gangster causing despair. It gave the actor a rare chance to showcase talent for playing villains he hadn’t shown before in his career. Working alongside Al Pacino who is also outstanding, Penn created a gangster drama that’s engaging. As strong as guns used by Carlito, it’s a captivating reminder of a commemorated actor that has manufactured great movies throughout his career which always give audiences dreams to commonly follow.
10. Gangster Squad
Sean Penn hasn’t always made great movies earning recognition. While most movies the actor has made are appreciated, a few have left audiences disappointed. Unfortunately, “Gangster Squad” falls into the latter category. Released in 2013, Ruben Fleischer’s crime thriller was a disaster. In the most shallow role of his career, Penn portrayed a gangster seeking to commit crimes in a city causing despair. Penn brought his usual charisma to the role, standing out as the bright spot of a bad movie. Although “Gangster Squad” is a bad movie, it honoured Penn’s enduring legacy. As strong as bonds between the gangster squad, it’s a breathtaking reminder of a commemorated actor that hasn’t lost abilities to leave audiences awed manufacturing movies that are rarely flawed which I will forever treasure for inspiring my love of Cinema I applaud.
The Film Buff 