Before leaving the Minneapolis hotel for the radio interview with NPR, David Lipsky knocks on David Foster Wallace's door which is numbered 1049. Later, when they are riding the elevator in silence, 17 rings can be heard as each floor is passed. The elevator finally stops at the 10th floor.
Before heading to the airport Lipsky is seen scraping snow off the windows. As they pull out a line of snow is visible at the base of the back window. Later while driving the snow is gone. As they pull into the airport the snow is back. Snow inconsistency continues when they return from the airport.
In regards to the scene where Mrs. Gunderson gives Mr. Wallace and Mr. Lipsky a car tour of Minneapolis sites: The Mary Tyler Moore statue on Nicollet Mall in Minneapolis, was not given to the City by TV Land until 2002. Also, it is not legal for cars to drive down Nicollet Mall.
When Lipsky and Wallace arrive at the airport's parking lot to fly to Minnesota, only the characters' car has residue of snow under the windshield. If this was truly the snow-filled environment the film portrays, surely other cars would also show signs of this.
The Sarah (Anna Chlumsky) was reading the famous 1996 political novel, Primary Colors, but the book was obviously not Primary Colors, as it was much too thick to be Primary Colors -- so it was obviously another, thicker book with a Primary Colors dust jacket slipped on.
When the two arrived at the airport parking lot at the start of their trip to the Twin Cities, they drive past a Subaru Outback with a body style that was not introduced until 2010.
When at the Mall of America, some of the rides shown in the mall were not present in 1996. Some logos corresponding to those rides (such as the new TMNT Animated TV Series) were also not present in 1996.
When returning from their trip and looking for their car at the airport's parking lot, many modern 2010s models trucks, SUVs and cars can be seen, even though the movie is set in 1996.
In one scene, a billboard for McDonald's can be seen at the far right of a gas station, designed at the time of the film's production. Though not clear to see, it uses the slogan "I'm lovin' it", which was not introduced until 2003.
As they drive into the airport parking lot a Honda Ridgeline can be seen parked under the 4F. The Ridgeline was not released until 2005.
When discussing movies to see at the Mall of America theater, David says that the film The Juror (1996) is based on a John Grisham novel. It's not a Grisham adaptation, and is actually based on a novel by George Dawes Green.