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Inspired by the death of singer Andrew P. Wood (Andrew Wood), the lead singer of Seattle bands 'Malfunkshun' and Mother Love Bone. Andy Wood (Andrew Wood) overdosed in January of 1990, right around the time when Cameron Crowe was working on this script.
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In the scene where Steve ('Campbell Scott (I)') is buying pregnancy tests and comes across the grocery cashier (Jeremy Piven), the cashier mentions that he knows him from "Mr. Deegan's class". Mr. Deegan is a teacher mentioned in Fast Times at Ridgemont High, which Cameron Crowe wrote.
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Citizen Dick's album name "Touch Me, I'm Dick" is a direct reference to the Seattle band Mudhoney and their song "Touch Me, I'm Sick".
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The rock band 'Nirvana' was supposed to contribute to the soundtrack but backed out.
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The pickup that hits the car with Steve and Linda says "Crowe Landscaping".
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Chris Cornell (of Soundgarden and Audioslave) saw a list of Citizen Dick song titles, all completely made up, which would appear briefly in the film and decided to pen songs to match each title. One of those songs, "Seasons", appears on the film soundtrack. Another, "Spoonman", was later recorded by Chris Cornell's band Soundgarden. It became a hit in 1994 and can be heard in a rough version (perhaps a demo) in the film when an unseen person is posting Citizen Dick flyers.
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A proposed alternate title for this film was "Come As You Are", named after the song by Nirvana.
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Jennifer Jason Leigh was originally cast as Linda but dropped out.
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In the "Expect the Best" scene, Debbie is offering some suggestions for her video look, one of which was what she called the "Edie Sedgwick". Edie Sedgwick is the second cousin of actress Kyra Sedgwick, who played Linda in this film.
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Contrary to popular belief, the film was already well underway when the celebrated "Seattle sound" became popular, rather than being designed as a vehicle to capitalize on its popularity. In fact, this film was supposed to begin production in 1984, right after The Wild Life but the project was delayed.
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Cliff is also wearing a shirt with Edie Sedgwick's face on it when he is delivering flowers.
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Paul Giamatti in one of his first films says one word: "What?"
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In one scene Matt Dillon's character is wearing a Green River shirt which is a reference to Stone Gossard and Jeff Ament's band before they were in Mother Love Bone, or Pearl Jam.
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The band playing in the bar is Alice in Chains.
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Campbell Scott's character is seen wearing a SubPop t-shirt, a well-known independent record company from Seattle which released many albums which became known as the "Seattle Sound", most notably Nirvana, Soundgarden, and Mudhoney.
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In an early scene at the coffee shop, Janet Livermore looks over a somewhat bizarre-looking customer's shoulder at a book that she is reading. Although the title is obscured, the book is "Psychotic Reactions and Carburetor Dung," a collection of pieces by the rock journalist Lester Bangs. Bangs was an inspiration and mentor for Cameron Crowe, as depicted in Almost Famous, in which Bangs is played by Philip Seymour Hoffman and advises the fictionalized version of the young Crowe.
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Jodie Foster and Mary Stuart Masterson were considered for the role of Linda Powell.
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Alice in Chains, playing the part of a sleazy bar band, perform the song "Would?" for the film prior to its live debut in May 1991 at the Starplex in Dallas. A year later in August 1992, a month after the film's release, "Would?" becomes Alice In Chains' biggest AOR hit to-date and "Singles" wins an MTV Movie Award for Best Movie Song.
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Steven drives an older red Saab fastback, the same car driven in Douglas Coupland's book Generation X. A book, like the movie, considered a touchstone for that generation.
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Tom Skerritt, who plays the mayor of Seattle, is a longtime resident of the city.
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Cameo 

Tim Burton:  video director
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Eric Stoltz:  the talking mime
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Chris Cornell:  man listening to car stereo when Cliff demos it for Janet.
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Stone Gossard:  Guitarist
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Jeff Ament:  Bassist/van driver
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Eddie Vedder:  Drummer
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Director Cameo 

Cameron Crowe:  reporter interviewing Matt Dillon.
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