It’s safe to say that Ryan Phillippe is one of the most adaptable actors working today. Phillippe’s acting career began when he appeared on ABC’s daytime soap One Life to Live. Billy Douglas, the role he played from 1992 to 1993, was the first gay teenager on a daytime soap series.
After leaving the program, Phillippe guest starred in shows like Matlock and Due South before landing a role in the slasher movie I Know What You Did Last Summer in 1997. The movie did well at the box office, leading to more opportunities for Phillippe in major films like 1998’s 54.
Over the past decade, Ryan Phillippe has focused nearly all his acting efforts on television programs like Shooter and Big Sky. This move was described by Phillippe in the following way, as reported by Cinema Blend:
The types of movies I made early in my career are virtually gone. I tended to exist in that $25m to $45m budget range. The way the film industry has [shifted], there’s just not as many movies being made outside of the tent-poles or the big action movies and Marvel and all of that… (Television) seems to be where the most interesting and layered stories are these days. It was certainly not that way when I began my career.
So then, let’s look at some of Ryan Phillippe’s most notable roles in cinema and television over the past three decades.
10. Straight A’s (2013)
Directed by James Cox and starring Anna Paquin, Ryan Phillippe, and Luke Wilson, Straight A’s is a romantic comedy directed by James Cox and produced by Jamie Adamic. Scott, played by Ryan Phillippe, is a volatile and unpredictable man who moves back to his hometown after being gone for a long time. Scott has been battling his issues, such as addiction and a string of poor choices.
Upon returning home, he is surprised to find his brother’s widow, Katherine (Anna Paquin), and their small boy waiting for him. Phillippe’s portrayal of Scott’s feelings, which include vulnerability and unpredictability, aptly conveys Scott’s inner turmoil and his yearning for a new beginning. His depiction of Scott exposes the character’s flaws while leaving room for development and evolution.
9. Shooter (2016 – 2017)
Shooter is an American drama series based on the 2007 film of the same name and the first three novels in Stephen Hunter’s Bob Lee Swagger series. Swagger, played by Ryan Phillippe, is a former Marine Corps Scout Sniper with MARSOC who is lured back into action after learning of a plot to kill the President.
Characteristically, Swagger is known for his superb marksmanship, tactical understanding, and dogged determination to uncover the truth. Phillippe conveys Swagger’s blend of stoicism, intensity, and empathy as he navigates a society riddled with betrayal and deception in his pursuit of justice.
8. Flags of our Fathers (2006)
Clint Eastwood’s Flags of our fathers is a film about the six men who hoisted the American flag at the Battle of Iwo Jima during World War II. Ryan Phillippe plays John “Doc” Bradley, a young Navy corpsman and one of the six soldiers who raised the end of the battle. Bradley and the other participants in the flag-raising ceremony are instantly hailed as national heroes and held up as an example of unwavering American patriotism.
Phillippe’s portrayal of Bradley goes beyond the heroic veneer to explore the mental toll of war, his struggle to come to terms with the horrors he observed while serving, and the expectations and obligations placed upon him. Phillippe’s portrayal of a character torn between heroic ideals and the brutal realities of war is both genuine and affecting.
7. Gosford Park (2001)
The 2001 film Gosford Park, directed by Robert Altman and written by Julian Fellowes, is a satirical black comedy mystery modeled by Jean Renoir’s classic French film La Règle du jeu. The film features the acting talents of Eileen Atkins, Bob Balaban, Alan Bates, Helen Mirren, Clive Owen, and Ryan Phillippe, among many other notable names. The plot follows a group of wealthy Britons, an American producer, and their staff as they spend a shooting weekend at the English rural mansion Gosford Park.
After a murder during a dinner party, the film shows the investigation from the perspectives of the staff and the guests. Henry Denton, played by Ryan Phillippe, is an American actor who joins the eventful weekend at the stunning English country estate of Morris Weissman by posing as his valet. Due to his charm and youthful vigor, Denton becomes entangled in the complex web of relationships and secrets between the affluent guests and their servants.
6. Crash (2004)
Officer Tom Hansen, played by Ryan Phillippe in the Academy Award-winning ensemble film Crash, is a young, idealistic police officer who must cope with the complexity of racial strife in Los Angeles. With his colleague Officer John Ryan (Matt Dillon), Hansen patrols the city streets, where he and Ryan encounter a succession of tales and characters that test their beliefs and reveal the prejudices that exist behind the surface of American culture.
Phillippe gives a subtle and compassionate performance as Officer Hansen, conveying the character’s moral ambiguities and internal problems as he fights against his prejudices and tries to restore order in a broken world. Paul Haggis produced, directed, and co-wrote the crime drama film, inspired by the actual 1991 carjacking of Haggis’ Porsche outside a Wilshire Boulevard video store. The movie stars an impressive cast, including Sandra Bullock, Don Cheadle, Brendan Fraser, Terrence Howard, Chris “Ludacris” Bridges, Thandiwe Newton, and Michael Peña.
5. I know what you did last summer (1997)
High school senior Barry Cox, played by Ryan Phillippe in the suspenseful horror thriller I Know what you did last summer, is a confident and athletic young man. After Barry and his friends hit a pedestrian on their way home from a party, they are embroiled in a nightmare scenario with Jennifer Love Hewitt’s Julie James, Freddie Prinze Jr.’s Ray Bronson, and Sarah Michelle Gellar’s Helen Shivers.
Barry first displays a belligerent and combative attitude, seeking to hide their dark secret due to the dread of being involved in a crime. Phillippe expertly depicts Barry’s spiral into paranoia and weakness as the consequences of their actions unfold and a mysterious killer begins pursuing them. Despite its mixed critical reception, the picture was a financial success, holding the top spot at the U.S. box office for three consecutive weeks.
4. 54 (1998)
Shane O’Shea, played by Ryan Phillippe in the drama film 54, is an ambitious young man who dreams of making it big in the glitzy world of Studio 54, a famous New York City nightclub in the 1970s. The club’s owner, Steve Rubell (Mike Myers), and renowned singer, Anita Randazzo (Salma Hayek), are just two of the many personalities Shane meets as he delves into the club’s crazy and hedonistic existence.
Phillippe’s portrayal of Shane shows how he develops as a person while he enjoys the decadent pleasures of the time and grooves to the era’s pulsating music. With all his boyish charm and relentless determination, Shane witnesses the ups and downs of the famed nightclub while confronting his own challenges and making choices that put his loyalty and honor to the test. Phillippe’s performance as Shane, a naive and wide-eyed innocent in a beautiful and alluring environment, is endearing and likable.
3. Cruel Intentions (1999)
Sebastian Valmont, played by Ryan Phillippe in the cult classic film Cruel Intentions, is alluring and manipulative. Valmont is a spoiled brat who enjoys the power and control that comes with his wealthy background. Playboy that he is, he makes a pact with his step-sister Kathryn Merteuil (Sarah Michelle Gellar) to seduce the pure and innocent Annette Hargrove (Reese Witherspoon). Phillippe does a fantastic job portraying Valmont’s development from a heartless womanizer to a man struggling with actual feelings and the repercussions of his actions.
Set in present-day New York City among privileged high school students, Cruel Intentions reimagines Pierre Choderlos de Laclos’s 1782 classic Les Liaisons Dangereuses. Although it initially had a modest budget, Columbia Pictures bought it and released it to theaters everywhere on March 5, 1999. Even though critics largely panned the picture, Gellar, Philippe, and Witherspoon stood out for their outstanding work.
2. Breach (2007)
FBI agent Robert Hanssen, who spied for the Soviet Union and then Russia for over two decades, is the inspiration for the espionage thriller Breach. Chris Cooper plays Hanssen, while Ryan Phillippe is FBI agent Eric O’Neill, who aids in Hanssen’s downfall. Young and driven, Eric O’Neill (Ryan Phillippe) works for the FBI.
O’Neill is in the middle of a dangerous game of cat and mouse as he attempts to collect evidence to bring charges against Hanssen. O’Neill steadily earns Hanssen’s trust with a combination of youthful vigor and acute intelligence, all while working covertly to disclose his true identity.
1. The Lincoln Lawyer (2011)
The Lincoln Lawyer is a legal thriller based on Michael Connelly’s 2005 novel of the same name. Played by Ryan Phillippe, Louis Roulet is a privileged young man accused of a heinous crime. Mickey Haller, portrayed by Matthew McConaughey, is Roulet’s defense counsel and doubts his story as the evidence mounts in the case.
Phillippe conveys the character’s wealthy upbringing and magnetic appeal while also alluding to a darker side. The attorney Haller faces a problematic adversary in Roulet, whose slick and manipulative attitude forces him to confront his own ethics and uncover the truth. Phillippe infuses the character with charisma and intensity, making for a fascinating interaction between Roulet and Haller as they navigate the court system’s many twists and turns.
