When meeting Woody Guthrie for the first time, Bob has fingerless gloves on as he places a capo on his guitar. In the reverse shot, the gloves are gone.
The position of debris fans threw at the band in the finale of the 1965 Newport Folk Festival changes shot to shot.
The watch on Alan Lomax's wrist has two different times during the planning meeting for the 1965 Newport Folk Festival.
When Sylvie leaves Newport and gets on a ferry, the fence that Bob and she speak through changes depending on the shot. Look at the gaps in between the fence links which increase and contract dramatically.
When Dylan is leaving Newport, he stops to watch Seeger putting away chairs. In the background is a cop standing in front of a police car. When seeing Dylan from Seeger's perspective, there are 2 cops in front of the police car.
Joan Baez asks Dylan if he's recorded Blowin' in the Wind after hearing it for the first time. This scene takes place in October 1962. In reality, he'd been playing the song at Village coffeehouses since at least April 1962. It was published in a May 1962 issue of Broadside, and a June 1962 issue of Sing Out! Dylan recorded it in July 1962. By October of that year, it wouldn't have been new to Baez or anyone on the folk scene.
The famous "Judas/I don't believe you/play it loud " exchange occurred not at the Newport Folk Festival but on May 17, 1966 in Manchester UK.
Dylan is seen watching the announcement of JFK's assassination on TV in NYC right before he performs at the 1963 Newport Folk Festival, but the festival was held in July 1963, and JFK was killed in late Nov 1963.
Dylan arrived in NYC in Jan of 1961, yet the car radio has a NY Giant's football game beginning and says the Giants are 8-3 at that point in the season and Y.A. Tittle is starting at QB as usual. There were no NFL games in Jan 1961, the championship game was played December 26 1960, and the NY Giant's season record that year was 6-4-2, their last game was Dec 18 1960, and Y.A. Tittle wasn't traded to the Giants until Aug 1961, and didn't start his first game until September 24 1961.
Dylan enters a record shop to look at how his first album is selling, but the image on the cover is not the same as the original.
When Johnny Cash performs on stage at the Folk Festival he greets the audience by simply saying 'Hello' and opening with 'Big River'. Throughout his entire career Cash would famously greet his audience by saying, 'Hello, I'm Johnny Cash' before performing 'Folsom Prison Blues'.
In the hospital at the beginning of the film, Dylan is shown tuning his guitar AFTER attaching the capo. You can't tune a guitar when the capo is attached, it needs to be tuned before.
At Newport 1965, stage monitors are visible when Bob and his electric band are performing. But no monitors were actually used at Newport that year, and they did not become common for performing musicians until a few years later.
Pete Seeger brings coffee to Dylan and others the morning of the Newport Folk Festival. The paper coffee cups have plastic lids that were not in use then, not even patented until 1967.
Joan's front cover on Time magazine was about a month after the end of the Cuban Crisis.
In several scenes, the same 1967 Volkswagen Beetle is visible in the background even though this film takes place between 1961-1965.
In a scene in which Bobby Neuwirth gets out of a cab to go to the Columbia Records studio, at the end of the block you can see a Burlington [Coat Factory] store. Not only is it a modern logo but Burlington Coat Factory wasn't founded until 1972 and didn't open stores in NYC until much later.
When "Like A Rolling Stone" is being performed, Mike Bloomfield (lead guitarist) is too far from the actual notes being played on the neck.