Bob Rafelson, the writer, director, producer and maverick who set the tone for the swinging, psychedelic 1960s with The Monkees, then was a pioneer in one of the most influential eras in the history of independent film, has died. He was 89.

Rafelson, who collaborated with Jack Nicholson on seven features, including the classics Easy Rider (1969), Five Easy Pieces (1970) and The King of Marvin Gardens (1972), died Saturday night (July 23) of natural causes at his home in Aspen, Colorado, his wife, Gabrielle, told The Hollywood Reporter.

Rafelson earned Oscar nominations for co-writing and producing Five Easy Pieces and then, for an encore, produced Peter Bogdanovich‘s breakthrough hit, The Last Picture Show (1971).

Along with his late partner Bert Schneider, Rafelson created The Monkees, the touchstone NBC show that debuted in 1966. He conceived the idea of a program that mimicked the exuberance of The Beatles, specifically the freewheeling energy of their 1964 film A Hard Day’s Night.

The series, produced by Raybert Productions, featured the comic misadventures of a struggling musical quartet seeking fame and fortune while living in Malibu. The foursome was selected from an open casting call announced with full-page ads, including one in THR. Stephen Stills was among the hundreds who auditioned. For years, an urban legend circulated that Charles Manson also had tried out. Davy Jones, Michael Nesmith, Micky Dolenz and Peter Tork ultimately were picked.

Colorful, fast-paced and filled with slapstick and silliness, The Monkees embodied the rebellious sensibilities of a younger generation. And though it lasted only two seasons and 58 episodes, it became a pop-culture phenomenon (and brought Rafelson and Schneider an Emmy in 1967 for outstanding comedy series).

In addition to guiding the sitcom as a producer and then executive producer, Rafelson directed several episodes. He also is credited with writing two of the shows that revolved around the group performing on tour.

Cast more for their personalities than their musical abilities, the quartet did possess talent. Jones was an English singer and actor who had gained fame playing the Artful Dodger on Broadway in Oliver. Nesmith and Tork knew their way around a guitar and were aspiring songwriters. Dolenz, a former child actor best known for the 1950s NBC series Circus Boy, had a great pop voice (and would learn how to play drums). But as they were not a natural combo, Rafelson and Schneider smartly hired musical producer Don Kirshner to oversee the music.

Kirshner in turn tapped some of the top songwriting talent of the era. Neil Diamond, Carole King, Harry Nilsson, John Stewart, Carole Bayer Sager, Neil Sedaka and the team of Tommy Boyce & Bobby Hart were among the contributors. The Monkees’ first four albums reached No. 1 on the Billboard charts, and the group landed six singles in the top 10, including “Last Train to Clarksville,” “I’m a Believer, “Pleasant Valley Sunday” and “Daydream Believer.”

The musical legacy that The Monkees left behind is arguably the band’s biggest impact.

After the series was canceled in 1968, Rafelson brought The Monkees to the big screen with Head (1968), his big-screen directing debut, as he and Schneider had secured a five-picture deal with Columbia.

“Bob was urged by his partners and friends not to make a movie with The Monkees,” his wife noted in a 2011 story in The Guardian about the band. “They felt he had done his work with them, and their audience was already defecting. But Bob felt he wanted to complete the cycle. He felt the truth of The Monkees’ story had not been told — their manipulation, protest and substantial talents. He felt the true story, in abstract [form], would be more than worth the telling.”

To create the screenplay, Rafelson teamed with Nicholson, then a B-actor and aspiring writer. Reportedly, the duo devised the storyline during a marijuana-fueled session in Ojai, with Nicholson then fashioning it into a script while under the influence of LSD.

Originally called Changes, the title was switched in a nod to the drug culture of the day. Rafelson and Schneider liked that, joking that they could market their subsequent feature with the slogan, “From the Guys Who Gave You Head.”

Critics found the movie a disjointed, confusing stream-of-consciousness excursion that deconstructed the pop persona that had made The Monkees stars.

Featuring a quirky cast that included Victor Mature, Annette Funicello, Teri Garr, Frank Zappa and Sonny Liston, Head ridiculed an array of subjects, including war, American values and the phoniness of Hollywood. Monkees fans were alienated by the group lashing out against the characters they played on TV. The adult audience they were trying to impress had long ago lost interest in what they considered a superficial pop band. Head was a box-office disappointment and stunted the Monkees’ popularity.

Later in The Guardian article, writer Dorian Lynskey added, “But Rafelson honestly believed it would work. ‘Bob was disappointed because he had hoped that the movie transcended the group’s name,’ Gabrielle says. He soon realized his error. At a Greenwich Village screening, hipsters lured in by the enigmatic posters walked out the minute The Monkees appeared. The reviews were savage. Of its $790,000 budget, it recouped just $16,111.”

Over the years, the film has gathered a cult following, helped by the word-of-mouth that it is best appreciated in an altered state.

The response to Head did not deter Rafelson. The second feature from Raybert Productions had been filming simultaneously and was nearing release. That was Easy Rider.

Directed by Dennis Hopper from a screenplay by Hopper, Peter Fonda and Terry Southern, Easy Rider rocked Hollywood when it hit theaters in summer 1969.

A counterculture commentary on America, Easy Rider starred Fonda and Hopper as pot-dealing hippies who, after a big score and a meeting with a drunken Lawyer (Nicholson), take to the road to go cross-country on their motorcycles. Along the way, they encounter the good and the bad of a nation.

Celebrating the free-spirited, drug-loving morés of the ’60s generation, Easy Rider was embraced by young filmgoers. Produced for less than a half-million dollars, it became the No. 3 grossing film of the year and made a star of Nicholson.

Easy Rider also proved to the studios that their stodgy star-driven, big-budgeted formula was in need of being replaced. And Rafelson was just getting started.

Raybert picked up a third partner, Stephen Blauner, and changed its name to BBS Productions (for Bob, Bert and Steve). Meanwhile, Rafelson was focusing on his second feature, Five Easy Pieces. True to his outsider leanings, the film tells the tale of a disconnected drifter, Bobby Dupea (Nicholson), who turns his back on his life of privilege and his talent as a piano prodigy to work on an oil rig. When his father becomes ill, he must return home to face what he has been rebelling against. In addition to directing and producing, Rafelson wrote the screenplay with Carole Eastman.

Five Easy Pieces was hailed as a cinematic masterpiece. Roger Ebert choose it as his best film of 1970, and it was nominated for four Academy Awards. Nicholson landed his second Oscar nom, cementing his stature as a leading man.

BBS Productions continued to usher in a new wave in indie film with such fare as The Last Picture Show; Drive, He Said (1971), which marked Nicholson’s directorial debut; the Oscar-winning antiwar documentary Hearts and Minds (1974); and the Rafelson-directed The King of Marvin Gardens (1972), starring Nicholson and Bruce Dern as brothers in an Atlantic City-set tale.

After completing its production deal with Columbia, BBS Productions stalled and Rafelson focused on making his own films. These efforts included Stay Hungry (1976), which featured newcomer Arnold Schwarzenegger, and The Postman Always Rings Twice (1981), which starred Nicholson and Jessica Lange in a stark, brutal remake of the 1942 MGM melodrama.

“If my films have anything in common,” he told the Los Angeles Times in 1986, “it’s that they tend to focus on characters who are struggling to overcome the burden of tradition in their lives.”

His career hit a snag, you might say, when he punched a Fox executive in the jaw and was fired from the job of directing Robert Redford in Brubaker (1980). He quit the business in 2002.

Robert Rafelson was born on Feb. 21, 1933, in New York. His father manufactured hat ribbons and his uncle was Samson Raphaelson, who wrote the short story and the Broadway play that served as the basis for Al Jolson’s The Jazz Singer (1927).

As a teenager, Rafelson rebelled against his father and refused to follow him into the textile business. “I was one of those guys that took on all comers,” he told the Times in 1997. “I started leaving home at the age of 14.”

Rafelson’s travels took him to Arizona, where he became a rodeo rider, and Acapulco, where he performed as a jazz musician. He studied philosophy at Dartmouth before being drafted into the U.S. Army. While stationed in Japan, he worked as a disc jockey, translated Japanese films and became an adviser to the Shochiku Co., offering opinions on films that he thought might do well in American theaters.

When Rafelson returned home, he secured a job in the mailroom of producer David Susskind’s company. He worked his way up to reader and then story editor for the Susskind anthology series Play of the Week and adapted several episodes. In 1961, he wrote an installment of the CBS fact-based drama The Witness.

In 1962, Rafelson came to Hollywood and worked as an associate producer on such ABC shows as The Greatest Show on Earth, starring Jack Palance, and Channing. On the latter, he butted heads with MCA mogul Lew Wasserman over the creative direction of the show. The argument ended with Rafelson sweeping the contents of Wasserman’s desk all over the floor, and he was fired.

But shortly after, he signed on as a producer for Screen Gems’ NBC adaptation of The Wackiest Ship in the Army, and it was here that he met Schneider. The following year, they formed Raybert, and soon Screen Gems would be sold on their idea for The Monkees.

Rafelson’s later directing efforts included Black Widow (1987), starring Debra Winger and Theresa Russell; the adventure tale Mountains of the Moon (1990); two more films starring Nicholson, Man Trouble (1992) and Blood and Wine (1997); and No Good Deed (2002).

In 1986, he helmed the music video for Lionel Richie’s mega-hit “All Night Long.”

While in high school, Rafelson began dating Toby Carr, and they married in 1955. She worked as a production designer with Rafelson on Five Easy Pieces, King of Marvin Gardens and Stay Hungry. They had two children. Peter is a songwriter, best known for the 1986 Madonna hit “Open Your Heart”; Julie was killed at age 10 when a propane stove exploded in the Rafelson home in Aspen.

Survivors also include his sons with Gabrielle, Ethan and Harper; daughter-in-law Karen; and a nephew.

This article was originally published by The Hollywood Reporter.