Despite Lelaina's anti-consumerism speech at the beginning, this film has a considerable amount of product placement and product references in the dialogue, including Gap, BMW, Diet Coca-Cola, Pringles, 7-Eleven (its Big Gulp drinks are seen throughout the film), Pizza Hut, Domino's Pizza, Evian, Camel Straight cigarettes, Snickers, McDonalds (Troy mentions a Quarter Pounder with Cheese as one of life's pleasures), Whole Foods Market, Continental Airlines, Cocoa Puffs, Infiniti (Nissan USA luxury automobile division), Ford Motor Company, and Minute Maid.
Quentin Tarantino had originally intended to include "My Sharona" (The Knack) on the soundtrack to Pulp Fiction (1994), but when he went to obtain the rights he found the song had already been licensed to this movie.
The scene in which Michael and Lelaina discuss the Big Gulp on the back of Michael's car was originally supposed to have the song "Beth" by 'KISS' playing. Ben Stiller couldn't secure the rights to the song so they opted for "Baby I Love Your Way" by Peter Frampton instead. Peter Frampton was an upstairs neighbor of Ben Stiller during filming of the movie.
Ethan Hawke performs "Marriage," by Gregory Corso, who was an intimate friend of Allen Ginsberg and other Beat poet/writers who were in turn friends of Winona Ryder's real-life parents. Corso eventually died in Minnesota, not far from Ryder's hometown of Winona, MN. And in 1985, in Houston, Texas where the movie takes place, feminist poet Hedwig Gorski published her work entitled "Could not get Gregory Corso out of my Car".
Original drafts of the script included a subplot involving Lelaina's alcoholic sister Patty, who was in rehab. A couple of those scenes were actually filmed but ended up getting cut. Patty was played by screenwriter Helen Childress' real-life sister, Patricia Childress.
Before filming began Janeane Garofalo was fired from the production because Ben Stiller did not like her attitude during rehearsal. Garofalo was rehired after Winona Ryder stepped in on her behalf. Garofalo stated later that she has a really poor work ethic and hates to rehearse.
Ethan Hawke was at this point unhappy with the direction his career was taking; the actor recalled that his career was in a lull after the buzz from Dead Poets Society (1989) had faded. Winona Ryder was a fan of his work and stipulated in her contract that her involvement in the film was dependent on Hawke starring opposite her. She chose Hawke after seeing him in A Midnight Clear (1992).
A Troy Dyer attended USC film school with Helen Childress, became a financial consultant in Wisconsin, and sued in 2005 for defamation. Childress claimed Dyer gave her permission to use his name, because he was straight-laced and conservative-the total opposite of the character. The case was settled to "everyone's mutual satisfaction," according to Dyer.
Lelaina sabotages Grant Gubler's program by tampering with his cue cards. At the beginning of the film, when delivering her Valedictorian speech at the Graduation ceremony, she herself experiences some cue card trouble, the end of her speech has gone missing ("The answer is.... I don't know.")
The film's producers saw the pilot episode for The Ben Stiller Show (1992) and approached Ben Stiller to direct it, but not act in it. He signed on to direct in 1992 and worked with Helen Childress for nine to ten months developing the script. Initially, Childress, working with producer Stacey Sher, had figured out the characters of Lelaina and Troy but could not come up with a credible character to complete the love triangle. Stiller suggested that he could play that third person. As a result, the Michael character changed from a 35-year-old advertising executive trying to market Japanese candy bars in America to a television executive in his twenties. They also changed the structure of the film. Originally, Vickie, Sammy and Troy had more fleshed out storylines, but Stiller felt that he could not tell them fully and decided to focus on the relationship between Lelaina and Troy.
After completing several period pieces, Winona Ryder was drawn to the film because she was looking "for something a little more contemporary because I really wanted to wear blue jeans for a change". She read the script in one sitting while making The House of the Spirits (1993) and "found it very true to life." She further speculated in an interview, "I think my character is very close to what I would probably have ended up as if I hadn't become an actress".
In 1991 producer Michael Shamberg had an idea to make a film about people in their twenties. He had read a screenplay entitled Blue Bayou written by Helen Childress on spec in 1990. He liked it and met with her where she proceeded to tell him about her life and friends and their struggle to find work during a recession in the United States at the time. For three years she wrote and rewrote the script, generating 70 different drafts. Childress decided to use her friends, their personalities and experiences as the basis for her film.
The filmmakers shot many of the exteriors in Houston (including a scene on top of the Two Shell Plaza building) where the film is set but most of the interiors were shot in Los Angeles, because it was cheaper to do so there.
Initially, the film did not perform as well at the box office as the studio had hoped. In six weeks it grossed $18.3 million, more than the film's $11 million production budget. Bruce Feldman, Universal Pictures' Vice-President of Marketing said, "The media labelled it as a Generation X picture, while we thought it was a comedy with broad appeal". The studio placed advertisements during programs chosen for their appeal to 12- to 34-year-olds and in interviews Ben Stiller was careful not to mention the phrase, "Generation X".
In the scene outside Johnie's Broiler Coffee Shop, Wynona Ryder & Janeane Garofalo are walking next to the neon Coffee Shop sign while talking. The two actresses are walking on an elevated platform, which the audience clearly can't see, as the sign is high off the street attached to the roof.