Neil Simon’s best films: From ‘The Odd Couple’ to ‘Biloxi Blues’

The influence of Neil Simon, who has died in New York at the age of 91, on American comic writing is incalculable. Before his work reached the big screen he achieved huge acclaim as a television writer, alongside Mel Brooks and Woody Allen, on Sid Caesar's endlessly influential Your Show of Shows and on The Phil Silvers Show.

That last sitcom, now usually thought of as just Bilko, generated some of the funniest episodes in US TV. A list of Bilko's 10 best episodes would alone justify Simon's position in the pantheon. He moved into theatre and then to film.

Nobody received a higher combined total of Emmy and Oscar nominations. Here are 10 essential Simon movies in order of release.

Barefoot in the Park (1967)

While "1967" was happening rebelliously elsewhere, zany Jane Fonda and stuffy Robert Redford – both equally beautiful – were squeezing themselves into a small flat in Greenwich Village. For good or ill, Fonda offers an early example of the Manic Pixie Dream Girl. Watch a clip here.

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The Odd Couple (1968)

First a play. Then a film. Then a TV series. Recast with two women. Staged with the original TV cast. Relaunched on TV with Matthew Perry. (Don't ask.) And so on. The best version of Simon's most durable work remains the original film with Jack Lemmon and Walther Matthau. Still a hoot. Watch the trailer here.

Sweet Charity (1969)

A rare musical from Simon – adapted from Fellini's Le Notti di Cabiria – Sweet Charity stars Shirley MacLaine as (euphemism alert) a dance-hall "hostess" who is misused by every heel in New York City. You couldn't get away with it now. The picture was one of many big-budget Hollywood musicals that bombed in the years after The Sound of Music, but it did give us Big Spender and If My Friends Could See Me Now. Problematic. Watch the trailer here.

The Out of Towners (1970)

A midwestern couple get lost in Manhattan. The sexual politics between Jack Lemmon's neurotic husband and Sandy Dennis's too-tolerant wife are a bit decrepit, but Arthur Hiller's film makes great use of its locations. Reminds us how frightened outsiders were of the city in those years. Watch the trailer here.

The Heartbreak Kid (1972)

Elaine May did brilliant work directing this acerbic tale of a klutz who, while on his honeymoon, falls for another intimidating, sophisticated woman. Although still oddly pitched – on his honeymoon, folks! – The Heartbreak Kid has aged better than many Simon films. Excellent early turn from Charles Grodin. Watch the trailer here.

The Sunshine Boys (1975)

George Burns won an Oscar for his role as half of a cranky comedy duo who come together for a tempestuous reunion. The film version by Herbert Ross does little to expand beyond its theatrical borders, but the interplay between Burns and Walter Matthau (who else?) is delightful. There is a TV adaptation with Woody Allen and Peter Falk that almost nobody has seen. Watch the trailer here.

The Prisoner of Second Avenue (1975)

Greeted with some bafflement on release, The Prisoner of Second Avenue is one of Simon's most serious comedies. Jack Lemmon stars opposite Anne Bancroft as a man coping with sudden unemployment in the middle of a particularly nasty New York heatwave. Features an early performance by Sylvester Stallone as a mugger. Watch the trailer here.

The Goodbye Girl (1977)

Richard Dreyfuss beat Richard Burton, nominated and strong favourite for Equus, to the Oscar for his enchanting performance as a pompous actor rooming grumpily with Martha Mason and her precocious daughter. Impossible to turn off once it begins on telly. Burton never did get that Oscar. Watch the trailer here.

Brighton Beach Memoirs (1986)

Many decades into his career, Simon had a critical smash with the autobiographical play on which this easy-going film was based. Set in a world we know also from Philip Roth and Woody Allen, the picture introduces us to a sensitive young Brooklyn man in a Jewish family before the war. Lovely turn from Blythe Danner as mom. Watch the trailer here.

Biloxi Blues (1988)

The sequel to Brighton Beach Memoirs – part of a trilogy completed by Broadway Bound – stars Matthew Broderick as a young man learning about life while undergoing basic training for the army. The great Mike Nichols, whose Broadway directorial debut was Barefoot in the Park, once again helps his old chum's words fizz. Watch the trailer here.