During filming, Casey Affleck mentioned to Kate Hudson that "Romeo and Juliet" by Dire Straits was one of his favorite love songs. Hudson secretly convinced director Risa Bramon Garcia to play the song during Affleck's and Hudson's final scene together as a surprise for him. Affleck didn't find out until he watched the movie at the premiere.
Christina Ricci said in an interview that while shooting in the East Village, the landlord of one of the buildings they shot in front of did not want the building featured in the movie, because she was personally against smoking, due to her father dying of lung cancer. She orchestrated several antics to sabotage shooting, including hanging a "NO SMOKING" sign in one of the windows, covering posts on the street with aluminum foil, and singing "Row Row Row Your Boat" during filming. She even almost punched out an extra for stepping onto the stoop during a shot, and walked towards camera with the "NO SMOKING" sign while singing.
Ben Affleck signed onto the film with the belief that he would support his younger brother Casey Affleck in his first leading role, while he played a small uncredited role. The older Affleck brother was surprised to see his name in the trades as a headline for signing onto the film.
First-time producer Betsy Beers was a huge Elvis Costello fan and told him on set that "Imperial Bedroom" was her favorite album. He was pleasantly surprised and told her, "No one ever mentions that album." He became instrumental in securing rights to songs they never could have afforded on their limited budget and even recommended little-known artists to whom the characters would likely be listening in 1981.
The title is a reference to a carton of cigarettes, ten packs per carton, twenty cigarettes per pack.
Elvis Costello: As himself. Costello first appears on screen as he moves between Paul Rudd's character Kevin and Courtney Love's character Lucy as they are having conversation, and Lucy suggests Kevin has sex on his birthday. Costello simply says, "Get out of the way, please," and walks off camera. Costello later appears in Polaroid photos of the New Years' party presented at the end of the film. In reality, Costello spent New Year's Eve, 1981 playing a concert with his band the Attractions at New York's Palladium theater on East 14th Street, some blocks north of where 200 Cigarettes (1999) takes place.