1. 'American Sniper'
Eastwood had the biggest hit of his career with "American Sniper", a film about real-life Navy S.E.A.L. sniper Chris Kyle, played by Bradley Cooper, who becomes a legend on the battlefield for his accuracy with a gun, but struggles to leave war behind him when he returns home.
2. 'Gran Torino'
Eastwood played Disgruntled Korean War vet trying to reform his teenage neighbour who attempted to steal his beloved 1972 Gran Torino car in this surprising hit.
Tom Hanks starred as Chesley "Sully" Sullenberger in the film about the pilot's daring emergency river landing in what was dubbed the Miracle on the Hudson.
4. 'Million Dollar Baby'
Eastwood took home his second Oscars for Best Director and Best Picture for "Million Dollar Baby", an emotional boxing drama about a woman training to become a professional boxer. Hilary Swank won Best Actress for her performance, and Morgan Freeman was award Best Supporting Actor.
5. 'The Bridges Of Madison County'
Eastwood starred opposite Meryl Streep in the tender romantic drama "The Bridges of Madison County" about a four-day love affair between a National Geographic photographer and a local woman whose husband and kids are away at the state fair.
6. 'The Mule'
Eastwood plays a 90-year-old Korean War veteran turned mule for a Mexican drug cartel, all while attempting to right the wrongs of his past.
Eastwood won Best Director and Best Picture for his classic revisionist western "Unforgiven", co-starring Morgan Freeman and Gene Hackman, about an old gunslinger heading out for one last job.
8. 'Mystic River'
A family tragedy drives a wedge between three childhood friends played by Sean Penn, Tim Robbins and Kevin Bacon in Eastwood's acclaimed and Oscar-nominated mystery drama.
9. 'A Perfect World'
A kidnapped boy befriends his kidnapper, played by Kevin Costner, an escaped convict on the run from a Texas Ranger played by director Clint Eastwood.
10. 'Space Cowboys'
Clint Eastwood went to space in the geriatric adventure film "Space Cowboys", bringing along fellow aging icons Tommy Lee Jones, Donald Sutherland and James Garner.
Morgan Freeman took on the role of Nelson Mandela in the sports drama about the South African leader's first term as president, enlisting Matt Damon's rugby player to win the 1995 Rugby World Cup.
12. 'Heartbreak Ridge'
Clint Eastwood directed and starred as Marine Gunnery Sergeant Tom Highway, who takes command of a recon platoon with a bad attitude, clashing with his superiors along the way.
Angelina Jolie goes up against the corrupt LAPD after her child is abducted and then replaced by an imposter in Eastwood's based-on-a-true-story drama.
Matt Damon starred in Clint Eastwood's spiritual drama about three different people touched by tragedy and death
15. 'J. Edgar'
Leonardo DiCaprio was nominated for Best Actor at the Golden Globes for his performance as longtime FBI director J. Edgar Hoover in Clint Eastwood's biopic.
16. 'Letters From Iwo Jima'
In the Oscar-nominated "Letters from Iwo Jima", Eastwood stepped into the shoes of the Japanese soldiers during WWII, creating a heartbreaking companion film to "Flags of Our Fathers", released the same year.
17. 'Sudden Impact'
Eastwood took over directing duties for "Sudden Impact", the fourth film in the popular Dirty Harry series.
Along with sending police officer Harry Callahan out of the city to a small town, the film also birthed the iconic catchphrase, "Go ahead make my day."
18. 'Jersey Boys'
From the Broadway stage to the silver screen, Clint Eastwood's adaptation "Jersey Boys" brought the joyous sound of Frankie Valli and The Four Seasons to delighted audiences around the world.
19. 'Flags Of Our Fathers'
In 2006, Clint Eastwood brought the WWII Battle of Iwo Jima to life on the big screen from the American soldiers' point-of-view in the harrowing, patriotic "Flags of Our Fathers". The acclaimed film starred Ryan Phillippe, Jesse Bradford, Adam Beach, Paul Walker and more.
20. 'The 15:17 To Paris'
Clint Eastwood brought to to the screen the true story of a foiled terrorist attack aboard a train in Europe, casting the real life heroes who stopped the attacker to recreate their extraordinary act.