Kris Kristofferson is a retired singer, songwriter, and actor. He is one of the most legendary people in Hollywood, who has had success in both singing and acting in his stellar career, up to the day he retired. He has also received a lot of huge songwriting hits for writing songs like “Help Me Make It Through The Night”, “Me and Bobby McGee”, and “For The Good Times.” His rugged looks, gravelly voice, and love for country music made him an instant fan favorite and hotshot crush of his generation.

After finishing his military service in 1965, he retired from the military as a helicopter pilot in Vietnam. After this, he did a lot of odd jobs before entering the music industry and later the acting industry. He made his acting debut with The Last Movie in 1971, which received a lot of love and praise for his acting. This was followed by an upward trajectory as he starred in many other movies, such as Dolphine Tale, solidifying his acting career. He is mostly known for his performance in A Star Is Born (1976) for which he received his first Golden Globe Award for Best Actor.

He retired from the industry in 2021, ending a stellar 55-year career and leaving some classics, and legendary movies and songs to be remembered by. To celebrate this amazing career, here are some of Kris Kristofferson’s best performances.

MOVIEWEB VIDEO OF THE DAY

6 The Sailor Who Fell from Grace with the Sea (1976)

     Embassy Pictures  

Directed by Lewis John Carlino, The Sailor Who Fell from Grace with the Sea is a drama-thriller movie starring Kris Kristofferson and Sarah Miles. The British movie is an adaptation of the Japanese novel of the same name by Yukio Mishima. The story is of a family drama, taking place when single parent Anne is swept off her feet by American sailor Jim Cameron. Jim Cameron is a typical soldier with a rugged yet handsome look. He is a very bold character in both the book and movie, and Kristofferson embodies that perfectly. He falls head over heels in love with Anne, and wants his life to revolve around hers, with a lot of risky public maneuvers.

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

5 Heaven’s Gate (1980)

     United Artists  

Directed by Michael Cimino, Heaven’s Gate is a drama noir movie revolving around disputes between landowners and immigrants in Wyoming in the ’80s. It is loosely based specifically based on the Johnson County War, starring Jeff Bridges, Kris Kristofferson, and Christopher Walken. Kris Kristofferson plays the role of James Averill, the sheriff of Jackson County. He becomes the middleman when the politically connected start disputes with the European immigrants. Kristofferson perfectly embodies the confusion and second-guessing nature of James as his character must make many decisions that are hard to make. The movie, over the years, has garnered a lot of support, despite the extremely low ratings at release. Kristofferson has specifically been praised extensively for his important participation in making the film what it is today.

4 Blade (1998)

     New Line Cinema  

Based on Marvel’s superhero, Blade was a legendary movie starring Wesley Snipes, Traci Lords, and Shannon Lee. Kris Kristofferson plays Blade’s mentor, Abraham Whistler. The movie follows the character of Blade, a half-human, and immortal with vampire strength. He must control his thirst in the movie to defeat his nemesis. Even though Kristofferson’s character was a minor one, he brought the excitement to the movie because of his character’s history and wit. He perfectly portrays the ruthless vampire hunter who does not feel a speck of sympathy for vampires but at the same time cares for Blade like a son. His character meets an unfortunate end as he kills himself after being infected with vampirism.

3 Alice Doesn’t Live Here Anymore (1974)

     Warner Bros. Pictures  

Directed by Martin Scorsese, Alice Doesn’t Live Here Anymore is a comedy-drama movie starring Ellen Burstyn, Alfred Lutter, Dianne Ladd, and Kris Kristofferson. The movie follows the story of a widow traveling through the Southwestern USA in search of a better life. Kristofferson plays the character of David, the mature and loving guy who Alice ends up falling in love with while pursuing her better life. He is a real father figure to Alice’s son and does nothing but give his endless love. Even beside this, their relationship is not the smoothest sailing one. Though David does not get a lot of lines, his presence is very dominant in the movie, keeping viewers hooked on the screen.

2 Pat Garrett and Billy the Kid (1973)

     Warner BrosMetro-Goldwyn-Mayer  

Directed by Sam Peckinpah, this movie was one of Kristofferson’s first few movies that really put him on the radar for his acting abilities. This Western-drama movie follows the story of negotiations between Pat Garrett, a renowned man, and Billy the Kid, a nefarious outlaw. Kristofferson plays the role of Billy the Kid, a feared man in the county, but also a dangerous one who a lot of people are after. Even though Pat and Billy are childhood friends, the lawman Garrett must abide by his duty. The movie received a lot of criticism over a loose script which did not offer a lot of depth, and many of the interesting scenes between the two childhood friends being shot in slow motion. However, even with these reservations, Billy the Kid, portrayed by Kristofferson, is the most endearing character on screen because of his snarky remarks.

1 A Star Is Born (1976)

Directed by Frank Pierson, A Star is Born was the masterpiece musical drama movie starring Barbara Streisand and Kris Kristofferson. It follows the story of a kindling musical romance between two singers, who have had a falling out with music. This complicated love story is an extremely known story and had a remake again in 2018, starring Lady Gaga and Bradley Cooper. Kristofferson plays the complex and downward-spiraling John Norman. Being a singer really helped him portray this character to perfection. He has the perfect voice for John’s character, with the deep country gritty tone in it. Along with singing in the musical, he also acts out all the emotions of the character simultaneously. His performance got him his first Golden Globe Award for Best Actor, which in popular opinion, was truly deserved.