Richard Lester Liebman was born to a Jewish family in Philadelphia, Pennsylvania. A child Prodigy, he began studies at the University of Pennsylvania at the age of 15. He started in television in 1950, working as a stage hand, floor manager, assistant Director and then Director in less than a year, because no one else was around who knew how to do the work.

Lester directed Action in the Afternoon an American western television series that aired live on CBS from February 2, 1953 to January 29, 1954. The series originated from the studios and back lot of WCAU, Channel 10 in Philadelphia, and was broadcast Monday through Friday regardless of the weather. The half-hour series aired variously at 3:30 pm or 4:00 pm, throughout its run. In 1953, Lester moved to London and began work as a Director in television, working for the low-budget producers The Danziger Brothers on episodes of Mark Saber, a half-hour detective series.

A short film Lester made with Spike Milligan and Peter Sellers, The Running Jumping & Standing Still Film (1959), was a favourite of the Beatles, and in particular John Lennon. When the band members were contracted to make a feature film, they chose Lester from a list of possible Directors. A Hard Day's Night (1964) showed an exaggerated and simplified version of The Beatles' characters, and proved to be an effective marketing tool. Many of its stylistic innovations survive today as the conventions of music videos, in particular the multi-angle filming of a live performance. Lester was sent an award from MTV as "Father of the Music Video."

Subsequent Lester films from the 1960s included Petulia (1968) with Julie Christie and a score by John Barry, as well as the darkly surreal anti-war movie How I Won the War co-starring Lennon, which he referred to as an "anti-anti-war movie"; Lester noted that anti-war movies still took the concept of war seriously, contrasting "bad" war crimes with wars fought for "good" causes like the liberation from Nazism or, at that time, Communism, whereas he set out to deconstruct it to show war as fundamentally opposed to humanity.

Lester directed the second Beatles film Help! (1965). Between the two Beatles films, Lester directed the first of several quintessential 'swinging' films, the sex comedy The Knack …and How to Get It (also 1965), the earliest of three films with actor Michael Crawford, which won the Palme d'Or at the Cannes Film Festival.

Although set in World War II, the movie is indeed an oblique reference to the Vietnam War and at one point, breaking the fourth wall, references this directly. Lester returned to his anti-war theme with the post-apocalyptic black comedy The Bed Sitting Room (1969) based on a play by Spike Milligan and John Antrobus.

In the 1970s, Lester directed a wide variety of films, including the disaster film Juggernaut (1974), Robin and Marian (1976), starring Sean Connery and Audrey Hepburn, and the period romance Cuba (1979), also starring Connery. However his biggest commercial successes in this period were The Three Musketeers (1973) and its sequel The Four Musketeers (1974). The films were somewhat controversial at the time because the producers, Alexander and Ilya Salkind, decided to split the first film into two after principal photography was completed. Many of the cast principals sued the Salkinds as a result, stating that they were only contracted to make one film.

Production on Superman II began before Superman was completed, and had to be halted to concentrate on getting the first movie completed. After the first Superman film was released in late 1978, the Salkinds went back into production on Superman II without informing Superman Director Richard Donner; they placed Lester behind the camera for the completion of the film. Although Donner had shot a majority of what was planned for the film, much of his footage was jettisoned or reshot during Lester's time on the project.

In 1984, Lester was awarded the MTV Video Vanguard Award.

In 1988, Lester reunited most of the Three Musketeers cast to film another sequel, The Return of the Musketeers, released the following year. During filming in Spain, actor Roy Kinnear, a close friend of Lester, died after falling from a horse. Lester finished the film, then unofficially retired from directing, returning only to direct the concert film of Paul McCartney entitled Get Back (1991). In 1993, he presented Hollywood UK, a five-part series on British cinema in the 1960s for the BBC.

Director Steven Soderbergh is among many who have called for a reappraisal of Lester's work and influence. He authored Getting Away With It, published in 1999, about Lester's career. which consists of interviews with Lester.

Gene Hackman, who played Lex Luthor, refused to return for the reshoots, so Lester instead used a stunt double and an impersonator to loop Luthor's lines onto footage of Hackman shot by Donner. Some of Donner's original footage was later integrated into television versions of the film. In November 2006, Donner's footage was reedited into Superman II: The Richard Donner Cut, consisting primarily of his footage with Lester's footage used only for scenes not shot during Donner's principal photography. Lester directed Superman III (1983), but this third installment was not as well received as its predecessors, yet was considered a box office success.