Factual error: In one scene a parked car is sitting along the street - it is a '68 Chevy, it has sidelights. Yet the film is set in 1962.
Factual error: When Hooker comes out of the diner there is a billboard advertisement to the right. It is for Ezra Brooks bourbon. Ezra Brooks brand wasn't created until 1957.
Factual error: Near the end of the chase, when Buddy is ramming the bad guys' car, the scene is supposed to take place in New Jersey as they just crossed the George Washington Bridge. However we see a road sign for NY 100/133, indicating they are back in New York state on the Taconic State Parkway.
Factual error: On the night of 19 October 1933 the railroad workers begin betting whether A-One will make it to Portland on the 19. A quick closeup of the money changing hands reveals the $1's to have the Great Seal reverse (introduced in 1935) plus the motto IN GOD WE TRUST (introduced in 1957). Also, the green-seal Federal Reserve Notes and the red-seal United States $2 notes are of the types first introduced in 1934.
Factual error: In the scene where Kananga's henchman Adam is being interrogated by Sheriff Pepper by his car at the riverside, the boat chase arrives and two boats jump clearly over head disillusioning Sheriff Pepper and allowing Adam to make a quick getaway. However, as Adam is getting away in his car, screeches can be heard coming from the tyres, but they are on a dry dirt road.
Factual error: Buford drives into his yard on Christmas morning and there are green leaves on the trees. Not in Tennessee, in winter!
Factual error: When Clint Eastwood first goes to the barber shop, the barber very deliberately sharpens his razor the wrong way, flipping the blade with its sharp edge against the strop - this would instantly dull the blade. No real barber would make this mistake, but it's a common movie error.
Factual error: The records played in the fairground sequence "Sealed with a kiss" by Brian Hyland and "Runaway" by Del Shannon date from the early sixties, while this part of the film is set in 1959.
Factual error: The kid is wearing a Texas Rangers baseball cap. The Rangers didn't come to Texas until 1972.
Factual error: The skywriting at the end of the film would have long drifted away by the time it is shown. The pilot has since landed on the road, taken off again and Jack & Ruby have made up, yet it is still in perfect formation.
Factual error: During the flashback explaining what happened to Su Lin she has an ugly bruise on her face less than a minute after being hit. Bruises usually take at least a few hours to develop like that.
Factual error: Anne Margaret is seen changing into pants, and as she's shown stepping into the pant leg she is wearing white pantyhose. Pantyhose wasn't invented at this time.
Factual error: Facing the mysterious fighter from Africa in his apartment, Shaft shoots him twice with no results. It is later revealed that he was wearing a bulletproof vest, but it's the overpowered movie kind: the guy doesn't suffer from the impact of the bullet in the slightest. Not just that: there's not a single hole or mark on his white robe in that scene. (00:08:40)
Factual error: The oil "drill" is actually an oil rig, meant to pump oil, not drill for it.