Screenwriter Richard Curtis was inspired by his own experience attending 65 weddings in an 11-year period, and began writing the script at age 34. It took him 17 drafts to reach the final version, and the film was originally conceived as 'Four Weddings and a Honeymoon' until Helen Fielding suggested adding the funeral theme.

Curtis based the origin of Charles and Carrie's romance on a real incident where he was propositioned by a fellow wedding guest, turned her down, and forever regretted it.

Alex Jennings was originally cast as Charles before funding fell through in 1992; he later appeared in a supporting role in the 2019 Hulu miniseries adaptation of the film. The producers auditioned roughly 70 actors for the role before choosing Hugh Grant.

Richard Curtis, who modeled Charles on himself, was initially opposed to casting Hugh Grant because he thought Grant was too handsome, and instead favored Alan Rickman, who refused to audition.

Jeanne Tripplehorn was originally cast as Carrie but dropped out after her mother died; the role was then offered to Marisa Tomei, who declined due to her sick grandfather, before Andie MacDowell was cast after reading the script while in London promoting Groundhog Day.

Andie MacDowell took a 75% pay cut to appear in the film, receiving only $250,000 upfront, but ultimately earned around $3 million thanks to the film's success.

The film was shot in just 36 days on a tight budget of £2.7 million, so extras had to wear their own wedding clothes and Rowan Atkinson played the vicar at two different weddings to avoid paying a second actor.

Future UK Home Secretary Amber Rudd was credited as 'Aristocracy Coordinator' for arranging real aristocrats, including the Marquess of Hartington and the Earl of Woolton, to appear as uncredited wedding extras wearing their own morning suits.

To make Hugh Grant look nerdier, the producers gave him shaggy hair, glasses, and deliberately ill-fitting clothes, while director Mike Newell encouraged him to stumble over his convoluted lines to give Charles a nervous, stammering quality; Grant, who suffered from hay fever during filming, thought his own performance was 'atrocious' at the time.

After an early test screening in Salt Lake City caused conservative Mormon city council members to walk out over the opening scene's repeated use of the word 'Fuck,' the filmmakers reshot the scene using the British swear word 'Bugger' for the American version.

The soundtrack featured Wet Wet Wet's cover of The Troggs' 'Love Is All Around,' which stayed at number 1 on the UK Singles Chart for fifteen weeks and became the ninth biggest-selling single in British history; the song was later reworked as 'Christmas Is All Around' for Richard Curtis's 2003 film Love Actually.

The film became the highest-grossing British film in history at the time, grossing $245.7 million worldwide, and its opening weekend gross in the UK set a record for a domestic production.

US distributor Gramercy Pictures objected during production to the film's explicit language and even its title, proposing alternatives such as 'True Love and Near Misses' and 'Skulking Around and Rolling in the Aisles,' none of which were used.

At the 25th anniversary, Curtis reunited director Mike Newell and the surviving cast for a Comic Relief short titled 'One Red Nose Day and a Wedding,' which revealed the involvement of Lily James and Alicia Vikander as the young couple only on the day it aired.