Continuity: When Charlie phones up Rob she has a big ring on her wedding finger (left hand), but when we cut back to her on the stairs the ring has moved to the equivalent finger on her right hand.
Continuity: When Rob talks about the five reasons why he misses Laura (on the Kinzie Street bridge, with the camera pointing south toward downtown) the shadows on the skyscrapers in the back differ between sentences.
Incorrectly regarded as goofs: "Janie Jones" by The Clash is listed as a "side one, track one." While it is indeed the first track on The Clash's British debut album, and the book was set in England, the film was moved to the USA, where the album started with "Clash City Rockers." But as record geeks, they would have been familiar with the British album as well, and could well have regarded it as the true debut album.
Incorrectly regarded as goofs: Rob mentions "Radiation Ruling the Nation" as one of his favorite side A, no. 1 tracks; he correctly identifies it as coming from the album "No Protection" (an album of remixes, and not the first release of the song). Arguably, this isn't a Massive Attack album, since it's actually remixes by Mad Professor. But the list is not restricted to debut albums, as some misinterpreted it.
Incorrectly regarded as goofs: Rob mentions the song "Landslide" while holding up the self-titled Fleetwood Mac album, which it appears on. The cover is similar to the cover for "Rumours", which confused at least one viewer.
Continuity: Rob's top button when confronting Laura.
Continuity: While sharing with the audience a list of books he has read, Rob puts a cigarette in the left side of his mouth and begins to light it. In the next shot he finishes lighting the cigarette and it is in the right side of his mouth.
Continuity: When Barry shows up with his top-five-records-to-play-on-a-Monday-morning "conversation stimulator" compilation tape, Rob's hair changes between shots during the ensuing argument.
Audio/visual unsynchronized: Dick plays Stiff Little Fingers' "Suspect Device" for Annaugh. Though he plays it from the "Inflammable Materials" LP, the version heard is the single version, different in a few ways from the LP version.
Continuity: While Barry is debating the word usage of "Yet" with Rob, he is putting away albums. One album sticks up from the collection in his hands, cut back and it is replaced or gone. Cut again and the album is again sticking out of the collection.
Continuity: When Caroline, the journalist, is speaking to Rob in the record store, her hairstyle changes.
Factual errors: When Rob switches on Bruce Springsteen's "The River", we see the record he's playing has an Impulse label. "The River", like all Springsteen records, was released on Columbia.
Revealing mistakes: During one of the phone conversations between Rob and Laura, Laura is shown in fairly tight close up. She is holding a "slimline" phone handset and at the extreme bottom edge of the frame you can see that although there is a phone cord socket on the phone, the cord is not attached. This is visible several times during the conversation.
Errors in geography: While engaging in a monologue about his relationship woes, Rob boards a Purple Line Express train of the Chicago Transit Authority. The Purple Line Express boards at the Howard Station on the far north side of Chicago and does not stop until the Belmont Station in Lakeview. However, just after Cusack boards the train, it passes Lincoln Hand Laundry and Graceland Cemetery; thus he must have boarded in Edgewater, well before Belmont, despite the fact that the train he was on does not stop in that neighborhood. Moreover, the scene ends with the Purple Line train (the "Loop" destination indicator is visible behind his head) descending into the subway. However, the Purple Line Express does not use the subway, but rather the elevated tracks, going into the Loop and turning back around and proceeding back through the city into the north suburbs.
Plot holes: Rob says he met Sarah after having "just been run over by Charlie" - who he dated during his sophomore year of college. However, when reminiscing about the circumstances of his and Sarah's relationship, he states that "?not many people are afraid of being left alone for the rest of their lives at 26". Of course, Rob may have entered college late, but he probably started at age 18 or 19 which would leave him, at the oldest, 21 when he broke up with Charlie and flunked out of college.
Factual errors: When Rob exits the funeral and walks out into the pouring rain, his suit is already wet when he walks out the door.
Factual errors: When Rob names some German musicians which inspired Barrys' band, he added Falco - but Falco was Austrian.
Errors made by characters (possibly deliberate errors by the filmmakers): When Rob and Barry are discussing 'Evil Dead 2', Barry mentions how unrealistic it is for a man in the 14th century to construct shotgun shells. He is actually referring to the sequel, 'Army of Darkness', not 'Evil Dead 2'.