Famous Actors Of The 20th Century

Without a doubt, the entertainment industry has most evolved in the past century. Films and television today are like never before – technologically advanced, emotionally real and contextually brilliant. Though the process involves a lot of artisans, from script writers and directors to cinematographers and editors, very few of us get into the depth of cinema. We generally are obsessed with the face of cinema – i.e. the actors. They are the people who bring to life characters, plot and story. Though the success or failure of a film depends on the combined effort of the cast and crew, it is generally actors who walk away with the adoration or pay the price for the success or failure of a film. 20th century boasts of a large pool of actors who have redefined cinema with their inherent acting skills and talent. With each outing, they have wowed the audience with their awe-inspiring performances. The past century entertainment industry saw some brilliant actors who were highly endowed and exceptional in their art. They were at the top of the game all through and gave some exceptional performances that have remained etched in the history of cinema; their films now being considered classics. Read through this section to know about some of the best known actors of the 20th century.

This ranking is based on an algorithm that combines various factors, including the votes of our users and search trends on the internet.

Vote for Your Favourite Actors Of The 20th Century

 1 
Keanu Reeves
(Television actor, Film actor, Actor, Film producer, Film director, Singer, Voice actor, Musician)

Keanu Reeves
58
Birthdate: September 2, 1964
Sun Sign: Virgo
Birthplace: Beirut, Lebanon

The star of John Wick, Speed and The Matrix films, Keanu Reeves has displayed his wide range as an actor, time and again. The humble Canadian actor has also famously given away his money to recognise the work of crew and to enable the production team to hire good actors.

 2 
Johnny Depp
(Actor and Producer Best Known for His Role in the 'Pirates of the Caribbean' Film Series)

Johnny Depp
45
Birthdate: June 9, 1963
Sun Sign: Gemini
Birthplace: Owensboro, Kentucky, United States

Johnny Depp is one of the most versatile and successful actors in Hollywood today. He wanted to become a musician and became actor by chance.  The star of Pirates of the Caribbean film series is known for selecting challenging roles that have the potential to amaze both audience and critics.

 3 
Leonardo DiCaprio
(One of the Highest Grossing Talented Actors in Hollywood Known for His Work in Biopics and Period Films)

Leonardo DiCaprio
62
Birthdate: November 11, 1974
Sun Sign: Scorpio
Birthplace: Los Angeles, California, United States

Leonardo DiCaprio is a name every movie lover reveres. An Oscar, a BAFTA, and 3 Golden Globes does not do justice to DiCaprio’s immensely skilful performances and his top-notch portrayals of addicts, historical figures and business tycoons. From epic dramas and romances to crime and political thrillers, DiCaprio has constantly left a mark in each of his films.

Recommended Lists:

 4 
Ryan Reynolds
(One of the Highest-Grossing Film Actors of All Time Best Known for His Role in 'Deadpool')

Ryan Reynolds
23
Birthdate: October 23, 1976
Sun Sign: Libra
Birthplace: Vancouver, Canada
The charismatic Canadian-American actor and film producer, Ryan Reynolds is best known for his work in Deadpool, Green Lantern and The Proposal. The talented star, who was once named by People magazine as the Sexiest Man Alive, has also featured in a music video, acted in a web series, lent his voice to animation films and successfully ventured into business.

 5 
Will Smith
(Actor)

Will Smith
76
Birthdate: September 25, 1968
Sun Sign: Libra
Birthplace: Philadelphia, Pennsylvania, United States

The charismatic, versatile and bankable American artist, Will Smith, tasted early success with rapping. A successful transition into films and television soon followed and made Smith a phenomenal success. With solid earnings, he has also frequently secured himself a place in the list of highest paid actors in world.

 6 
Tom Cruise
(One of the Highest-Grossing Box Office Stars of All Time)

Tom Cruise
76
Birthdate: July 3, 1962
Sun Sign: Cancer
Birthplace: Syracuse, New York, United States

Actor-producer, Tom Cruise, is an international superstar, heartthrob of millions and is a recipient of numerous awards. The Mission: Impossible star has been one of the most bankable and versatile Hollywood actors since 1980s. Interestingly, he once aspired to be a priest but is now amongst the highest paid actors in the world.

 7 
Robin Williams
(Actor & Comedian Best Known for His Roles in 'Mork & Mindy ', 'Popeye' and 'Good Will Hunting')

Robin Williams
44
Birthdate: July 21, 1951
Sun Sign: Cancer
Birthplace: Chicago, Illinois, United States
Died: August 11, 2014

One of the finest comedians of all time, Robin Williams began his career as a stand-up comedian and soon moved to act in television and films. Though widely recognised for his comedic skills, the immensely talented Williams proved his versatility by taking up and successfully performing more serious roles in films like Good Will Hunting and The Fisher King.

You May Like

 8 

Robert Downey Jr.
29
Birthdate: April 4, 1965
Sun Sign: Aries
Birthplace: Manhattan, New York, United States
Robert Downey, Jr is an American actor who is best known for his performances in the movie Chaplin as well a in the Iron Man and Sherlock Holmes film series. The son of filmmaker Robert Downey, Sr, he entered the world of acting early, fought a successful battle with drug and alcohol addiction and proved his talent and versatility with his impressive body of work.

 9 
Brad Pitt
(Actor)

Brad Pitt
40
Birthdate: December 18, 1963
Sun Sign: Sagittarius
Birthplace: Shawnee, Oklahoma, United States

Counted among the most influential and powerful people in the American entertainment industry, Brad Pitt is an actor and film producer who has appeared in many big-budget productions. He was cited as the world’s most attractive man for several years. He is also involved in various philanthropic and humanitarian endeavors.

 10 
Heath Ledger
(Actor, Photographer)

Heath Ledger
28
Birthdate: April 4, 1979
Sun Sign: Aries
Birthplace: Perth, Australia
Died: January 22, 2008

An Australian actor, Heath Ledger grabbed limelight in America with the teen comedy 10 Things I Hate About You. However, it was role in Brokeback Mountain that made him a star and earned him comparisons with greats actors like Marlon Brando. The brilliant actor gave his last performance as Joker in The Dark Knight which became a massive success.

 11 

Sean Connery
28
Birthdate: August 25, 1930
Sun Sign: Virgo
Birthplace: Fountainbridge, Edinburgh, Scotland
Died: October 31, 2020

The first person to play James Bond on screen, Scottish actor Sean Connery went on to star in seven films of the franchise. The role catapulted him to international fame, but this charismatic actor was not restricted to his iconic role. He also tasted critical and commercial success in other productions including Murder on the Orient Express and The Untouchables

 12 
Harrison Ford
(One of The Highest-Grossing Actors in North America)

Harrison Ford
32
Birthdate: July 13, 1942
Sun Sign: Cancer
Birthplace: Chicago, Illinois, United States

With an extensive career spanning six decades, veteran actor Harrison Ford is a major figure in Hollywood. The recipient of many prestigious awards, including the Cecil B. DeMille Award, he is one of the highest-grossing domestic box office stars of all time. Besides acting, he is a licensed pilot of both fixed-wing aircraft and helicopters.

 13 

Matthew McConaughey
34
Birthdate: November 4, 1969
Sun Sign: Scorpio
Birthplace: Uvalde, Texas, United States

Born into a family of mixed ancestry in Texas, actor Matthew McConaughey had an interesting childhood. He played sports as a young boy and aspired to become a lawyer. However, he ultimately changed course to venture into acting, a field where he was able to make a mark with his brilliant performances. He is also a producer.

 14 
Joaquin Phoenix
(One of the Greatest Actors of the 21st Century)

Joaquin Phoenix
57
Birthdate: October 28, 1974
Sun Sign: Scorpio
Birthplace: San Juan, Puerto Rico

Award-winning actor Joaquin Phoenix is widely regarded as one of the most talented actors of his generation. In his career of four decades, he has starred in numerous films playing characters that have become memorable. These include movies like Gladiator, Joker, Walk the Line and Her. The acclaimed actor is also a social activist, environmentalist, animal rights activist and producer.

 15 

Daniel Craig
14
Birthdate: March 2, 1968
Sun Sign: Pisces
Birthplace: Chester, Cheshire, England

An English actor who achieved international fame when he began starring as the title character in the James Bond film series, Daniel Craig is known for his rugged good looks and raw sex appeal. Beginning his career in the early 1990s as a theater actor, he soon ventured into cinema as well. He has been nominated for many awards.

 16 
Hugh Jackman
(Actor, Producer)

Hugh Jackman
19
Birthdate: October 12, 1968
Sun Sign: Libra
Birthplace: Sydney, Australia

Australian actor Hugh Jackman’s Hollywood debut in the film X-Men made him a transatlantic actor and he went on to do the X-Men film series from 2000 to 2018. Some of his other prominent films are Kate & Leopold, Les Misérables, The Greatest Showman, The Prestige and Australia. He is also a singer, songwriter and a dancer.

 17 
Robert De Niro
(One of the Best and Most Eccentric Actors of His Generation)

Robert De Niro
23
Birthdate: August 17, 1943
Sun Sign: Leo
Birthplace: Greenwich Village, New York, United States

Amongst the best actors of his generation, Robert De Niro is known for his exceptional method acting skills. His formidable acting talent has impressed audience and critics alike in movies like Mean Streets, The Godfather Part II and Meet the Parents. The talented actor has also been applauded for his directorial skills in A Bronx Tale and The Good Shepherd.

 18 

Nicolas Cage
20
Birthdate: January 7, 1964
Sun Sign: Capricorn
Birthplace: Long Beach, California, United States

Counted among the top movie stars in the late 1990s, actor Nicolas Cage continues to be a key figure in Hollywood. In a career spanning around four decades, he has appeared in a variety of mainstream films. The recipient of numerous awards, he has won an Academy Award and a Golden Globe among others. He often donates to charities.

 19 
Patrick Swayze
(Known For His Role in 'Dirty Dancing' & 'Ghost')

Patrick Swayze
22
Birthdate: August 18, 1952
Sun Sign: Leo
Birthplace: Houston, Texas, United States
Died: September 14, 2009

Patrick Swayze, the American actor, dancer, singer and songwriter, was very popular during the 1980s. His movie the ‘Dirty Dancing’ catapulted him to stardom. Ghost was another of his hit films. Swayze died in September, 2009, at the age of 57 due to pancreatic cancer. His final role was that of a FBI Agent in the television series ‘The Beast’.

 20 
Liam Neeson
(Starred as Oskar Schindler in 'Schindler's List')

Liam Neeson
18
Birthdate: June 7, 1952
Sun Sign: Gemini
Birthplace: Ballymena, Northern Ireland

The recipient of multiple awards, actor Liam Neeson has been ranked among  the '100 Sexiest Stars in Film History'. One of the highest-grossing actors of all time, he first rose to prominence in the 1990s with his title role in the epic drama film Schindler's List. Since then, he has appeared in many other critically acclaimed films.

 21 
Denzel Washington
(One of the Most Profound Actors Best Known for His Academy Award Winning Movie 'Training Day')

Denzel Washington
22
Birthdate: December 28, 1954
Sun Sign: Capricorn
Birthplace: Mount Vernon, New York, United States

Actor, director, and producer, Denzel Washington, is famous for portraying strong real-life characters like anti-apartheid activist, Steve Biko, and human rights activist, Malcolm X, in films. Well-built and ruggedly handsome, he became the first black star to be named the Sexiest Man Alive in 1996. 

 22 
Al Pacino
(One of the Few Actors To Achieve the 'Triple Crown of Acting')

Al Pacino
16
Birthdate: April 25, 1940
Sun Sign: Taurus
Birthplace: East Harlem, New York, United States

Considered one of the greatest actors, Al Pacino gained wide acclaim and recognition for his portrayal of Michael Corleone in the movie, The Godfather in 1972. He’s been a part of many successful and iconic films and won an Oscar for playing a blind military veteran in the movie Scent of a Woman. Pacino has three children, but has never been married.

 23 
Matt Damon
(One of the Highest-Grossing Actors of All Time)

Matt Damon
25
Birthdate: October 8, 1970
Sun Sign: Libra
Birthplace: Cambridge, Massachusetts, United States

One of the biggest Hollywood stars of his time, Matt Damon is one of the highest-grossing actors of all time. Saving Private Ryan, The Talented Mr Ripley, The Martian and The Departed are some of his notable films. He has also been part of the highly successful Bourne franchise and the Ocean's trilogy.

 24 
Charlie Chaplin
(Actor, Comedian)

Charlie Chaplin
18
Birthdate: April 16, 1889
Sun Sign: Aries
Birthplace: Walworth, London, England
Died: December 25, 1977

Cinema lovers around the world hold Charlie Chaplin in high esteem. One of the biggest stars of the silent film era and an icon, he left the audience in splits with his comedic performances. Even today, his performances in movies like Modern Times and The Gold Rush are considered classic. The legendary actor was also a writer, director and producer.

 25 

Samuel L. Jackson
19
Birthdate: December 21, 1948
Sun Sign: Sagittarius
Birthplace: Washington, D.C., United States

Actor and producer, Samuel L. Jackson is widely regarded as one of the most popular actors of his generation. A highly prolific actor, he has appeared in over 150 films and is especially known for his roles in Quentin Tarantino films. Besides acting, he has voiced for several animated films, television series, and video games.

 26 
Christian Bale
(Known for Recurring Physical Transformations to Play His Roles)

Christian Bale
18
Birthdate: January 30, 1974
Sun Sign: Aquarius
Birthplace: Haverfordwest, Pembrokeshire, Wales

After bagging his first starring role when he was just 13, actor Christian Bale proceeded to become one of the finest actors of his generation in the ensuing years. Known for his commitment to his craft, he is considered one of the most versatile and talented actors today. He is also popularly regarded as a male sex symbol.

 27 

George Clooney
24
Birthdate: May 6, 1961
Sun Sign: Taurus
Birthplace: Lexington, Kentucky, United States
Multiple award winning actor, producer, writer and director, George Clooney rose to fame with a medical drama ER and has since then established himself as a bigtime star with movies like Syriana, Good Night, and Good Luck and Ocean's Eleven trilogy. The living legend is also known for his humanitarian work and support to numerous social and political causes.

 28 
John Wayne
(A Popular Icon During Hollywood's Golden Age)

John Wayne
14
Birthdate: May 26, 1907
Sun Sign: Gemini
Birthplace: Winterset, Iowa, United States
Died: June 11, 1979

Famous for his roles in Western films in the mid-20th century, actor John Wayne was among the top box office draws for three decades. In a career spanning over half a century, he starred in 142 motion pictures. Upon his death, he came to be recognized as “an enduring icon who symbolized and communicated American values and ideals.”

 29 
Danny DeVito
(Actor, Director, Producer)

Danny DeVito
14
Birthdate: November 17, 1944
Sun Sign: Scorpio
Birthplace: Neptune Township, New Jersey, United States

An award-winning actor, Danny DeVito overcame a rare genetic disorder called Fairbank's disease to become an influential figure in the American film industry. Along with Michael Shamberg, he founded a production company called Jersey Films, which went on to produce films like Pulp Fiction. He was honored with a star on the Hollywood Walk of Fame in 2011.

 30 
Jack Nicholson
(The Most Nominated Male Actor in the History of Academy Awards)

Jack Nicholson
19
Birthdate: April 22, 1937
Sun Sign: Taurus
Birthplace: Neptune City, New Jersey, United States

From being a stage and B movie actor, Jack Nicholson went on to become one of Hollywood’s most versatile actors and a huge star. The three time Academy award winning legendary actor has, in his six decades career, delivered performances that have become iconic. His notable performances include One Flew Over the Cuckoo’s Nest and As Good as It Gets.

 31 

Ewan McGregor
15
Birthdate: March 31, 1971
Sun Sign: Aries
Birthplace: Perth, Scotland

A critically acclaimed actor, known for working in many small independent films, Ewan McGregor’s first notable film was Shallow Grave, followed by Trainspotting which propelled him to stardom. Films like Emma, A Life Less Ordinary and Moulin Rouge and the role of Obi-Wan Kenobi in the three Star Wars prequels, plus the television series Fargo are his other notable works.

 32 
Jamie Foxx
(Best Known for His Portrayal of Ray Charles in the Biopic 'Ray')

Jamie Foxx
20
Birthdate: December 13, 1967
Sun Sign: Sagittarius
Birthplace: Terrell, Texas, United States

Actor, singer-songwriter, and comedian, Jamie Foxx became internationally famous for his portrayal of Ray Charles in the biographical film Ray, a role that earned him an Academy Award. He is also known for hosting his own television sitcom, The Jamie Foxx Show. Besides acting, he is also a Grammy Award-winning musician who has released four albums.

 33 
Mel Gibson
(Known For His Action Hero Roles)

Mel Gibson
19
Birthdate: January 3, 1956
Sun Sign: Capricorn
Birthplace: Peekskill, New York, United States

Actor and director, Mel Gibson is famous for action films like Lethal weapon. His directorial venture, Braveheart, in which he acted too, won him the Oscars for Best Director and Best Picture. However, his alcoholism issues, drunken driving arrest and his anti-Jew statements landed him in trouble due to which he took a hiatus from Hollywood for a decade.

 34 
Marlon Brando
(One of the Most Influential Actors of the 20th Century)

Marlon Brando
13
Birthdate: April 3, 1924
Sun Sign: Aries
Birthplace: Omaha, Nebraska, United States
Died: July 1, 2004

One of the greatest movie actors of all time, heartthrob of millions of women around the world, and a cultural icon, who had immense influence on actors of future generations, there are very few like Marlon Brando. In a career spanning six decades, Marlon Brando delivered critical and commercial successes in movies like A Streetcar Named Desire and The Godfather.

 35 

Gary Oldman
14
Birthdate: March 21, 1958
Sun Sign: Aries
Birthplace: New Cross, London, England

Gary Oldman is an English actor who can be best described as a chameleon, for his remarkable ability to imbibe the traits and mannerisms of the character he portrays. Whether playing a Cold War spy or a Sci-fi villain or Winston Churchill, this acting genius has earned the praise of millions of fans around the world.

 36 
Michael Douglas
(One of the Most Popular and Critically Acclaimed Actor of His Generation)

Michael Douglas
20
Birthdate: September 25, 1944
Sun Sign: Libra
Birthplace: New Brunswick, New Jersey, United States

One of the most decorated American actors, Michael Douglas is popular for playing a variety of roles. Apart from acting, Michael Douglas has received attention for his political activism and humanitarianism. A cancer survivor, Douglas serves as an inspiration to those suffering from the disease; he recovered from stage IV tongue cancer.

 37 

Kevin Costner
14
Birthdate: January 18, 1955
Sun Sign: Capricorn
Birthplace: Lynwood, California, United States

Actor, film director, and producer, Kevin Costner, is a much-decorated Hollywood with two Academy Awards and two Golden Globe Awards to his name. Even though he never dreamed of a career in films as a youngster, fate ultimately led him to Hollywood where he made a successful career. He is also a singer in a country rock band.

 38 

Patrick Stewart
9
Birthdate: July 13, 1940
Sun Sign: Cancer
Birthplace: Mirfield, Yorkshire, England

Eminent British actor, Patrick Stewart, is best known for his work in television series, Star Trek: The Next Generation, and four films associated with it. Another project that brought him immense recognition was the X-Men film series. A passionate stage artist, he has devoted considerable time to stage and delivered strong performances in Anthony and Cleopatra and A Christmas Carol

 39 
Anthony Hopkins
(Known for His Role as ‘Hannibal Lector’ in Jonathan Demme's ‘The Silence of the Lambs’)

Anthony Hopkins
20
Birthdate: December 31, 1937
Sun Sign: Capricorn
Birthplace: Margam, Wales, United Kingdom

Highly renowned Welsh actor, Anthony Hopkins is best known for his portrayal of a cannibalistic serial killer in the movie The Silence of the Lambs. The portrayal earned him prestigious awards and also a place in the list of best villains of all time. Other notable films of the celebrated character actor include Remains of the Day, Nixon and Amistad.

 40 

Paul Newman
16
Birthdate: January 26, 1925
Sun Sign: Aquarius
Birthplace: Shaker Heights, Ohio, United States
Died: September 26, 2008

One of the most celebrated actors of the 1960s and 1970s, Paul Newman was a multi-faceted man. Apart from winning acting accolades, such as the Academy Award, he had also won many championships as a driver as part of the Sports Car Club of America. Also known for his philanthropy and political activism, Newman founded many nonprofit organizations.

 41 

Brendan Fraser
15
Birthdate: December 3, 1968
Sun Sign: Sagittarius
Birthplace: Indianapolis, Indiana, United States

Brendan Fraser is the quintessential comical action hero of Hollywood. As a result of the stunts performed by him in movies, he has had to undergo many surgeries, including a laminectomy and partial knee replacement. He is also a successful amateur photographer and serves on the board of directors for a non-profit humanitarian organization called FilmAid International.

 42 
James Dean
(Actor)

James Dean
11
Birthdate: February 8, 1931
Sun Sign: Aquarius
Birthplace: Marion, Indiana, United States
Died: September 30, 1955

Best remembered for his role in the film, Rebel Without a Cause, actor James Dean was a cultural icon of teenage disillusionment. Despite having a difficult childhood, he was an exceptional student. He began acting as a young man and was quite successful. Sadly, he was killed in a car crash at the young age of 24.

 43 
Ralph Fiennes
(English Actor Best Known for His Films: 'Schindler's List', and 'The English Patient' )

Ralph Fiennes
16
Birthdate: December 22, 1962
Sun Sign: Capricorn
Birthplace: Ipswich, England

A Tony Award recipient, Ralph Fiennes is one of the most respected English actors of the current generation. He is known for playing important roles in notable films, such as the Harry Potter and James Bond film series. A Stanislavsky Award recipient, he is also known for his work behind the camera.

 44 
James Earl Jones
(One of the Greatest Actors in American History)

James Earl Jones
14
Birthdate: January 17, 1931
Sun Sign: Capricorn
Birthplace: Arkabutla, Mississippi, United States

A veteran actor with a career spanning more than seven decades, James Earl Jones has been described as "one of America's most distinguished and versatile" actors. He initially aspired to be a doctor but fate had other plans for him. He began his career as a stage actor and soon joined films as well.

 45 

Richard Gere
10
Birthdate: August 31, 1949
Sun Sign: Virgo
Birthplace: Philadelphia, Pennsylvania, United States

Richard Gere's performance in the movie American Gigolo cemented his position as a sex symbol in the 1980s. He also established himself as a leading man, becoming one of Hollywood's most bankable and popular actors during the '90s. One of the most dedicated actors, he learned karate for his role in An Officer and a Gentleman and tap dance for Chicago.

 46 

Christopher Walken
10
Birthdate: March 31, 1943
Sun Sign: Aries
Birthplace: Astoria, New York, United States

Christopher Walken is one of the highest-grossing American actors as his films have generated over $1 billion in the US alone. He has a unique distinction of appearing in over 100 films and TV programs. A man of many talents, Christopher Walken is also known for his comedic, singing, screenwriting, directing, and dancing skills.

 47 
Charles Robert Redford Jr.
(Actor, Director and the Founder of the ‘Sundance Film Festival’)

Charles Robert Redford Jr.
14
Birthdate: August 18, 1936
Sun Sign: Leo
Birthplace: Santa Monica, California, United States

Charles Robert Redford Jr. is a retired actor, activist, and director. He is credited with founding the Sundance Film Festival and was named in Time magazine's list of 100 most influential people in the world in 2014. For his contributions to arts, Charles Robert Redford Jr. was honored with the Presidential Medal of Freedom in 2016.

 48 
James Stewart
(Ranked 3rd on the List of 'Greatest American Male Actors')

James Stewart
11
Birthdate: May 20, 1908
Sun Sign: Taurus
Birthplace: Indiana, Pennsylvania, United States
Died: July 2, 1997

Best known for his everyman screen persona, James Stewart was ranked third in the greatest American male actors list published by the American Film Institute (AFI) in 1999. During his 55-year acting career, he displayed strong morality both on and off the screen, as a result of which he epitomized the ideal American man of the 20th century.

 49 
Kirk Douglas
(17th-greatest male star of Classic Hollywood cinema)

Kirk Douglas
20
Birthdate: December 9, 1916
Sun Sign: Sagittarius
Birthplace: Amsterdam, New York, United States
Died: February 5, 2020

The quintessential American action hero of the 1950s, Kirk Douglas remained one of the most bankable stars of Hollywood throughout the decade. Regarded as one of the greatest actors of classic Hollywood cinema, Kirk Douglas was a man of many talents. Also known as a writer and philanthropist, he was honored with the Presidential Medal of Freedom in 1981.

 50 
Kiefer Sutherland
(Played Lead Role in TV Series '24')

Kiefer Sutherland
7
Birthdate: December 21, 1966
Sun Sign: Sagittarius
Birthplace: London, England

The son of famous Canadian actors, Shirley Douglas and Donald Sutherland, Kiefer Sutherland followed in his parents' footsteps to become a famous actor. Apart from being a respected and decorated actor, Kiefer is also one of the controversy's favorite children, having been on the wrong side of the law several times.