Character mistake: When Tommy is being shown his new office the glass reads "Thomas R. Callahan III, " but when Tommy is introduced as the new President of the company he is introduced as "Tom Callahan, Jr." which would be his dad. (00:11:35 - 02:11:55)

Tommy Boy (1995)
1 suggested correction
Directed by: Peter Segal
Starring: Dan Aykroyd, Brian Dennehy, David Spade, Chris Farley, Bo Derek
Revealing mistake: When Tommy is trying to bend the car door back you can see a wire holding the door in place so that Tommy can hit it as hard as he wants and it won't go back in place.
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Suggested correction: It is possible (probably not common) to be a "III" and a "Jr." If you are named after your father, and he is still alive you are a Junior. If you both share the name with another member up the family tree say your great grandfather, then your father would be a "II" and you would be a "III." But since your father is still alive, you can still go by junior. I've known one person in this situation.
I guess you missed the part of the movie where his father died. He's made the new president because his dad is dead, not alive, negating your main point.
Bishop73
His dad literally just died, and most people don't know the specifics of the naming rules. That would be a character mistake of the person introducing him.
When Tommy is made president and introduced, that's at the end of the film. So, no, his dad didn't literally just die. Plenty of time passed. But the correction is wrong on its premise, but that's not to say a different argument couldn't be made why the mistake is wrong.
Bishop73