Borrowing the thread title...

How should I enter the following credit:  Carroll Gibbons and His Orchestra

1.  Carroll Gibbons and His O 
2.  Carroll // Gibbons and His Orchestra
3.  Carroll // Gibbons and His // Orchestra

I'm pretty sure that the first one is likely correct by the rules, since this is basically a band, but the field length cuts off a the O, so I'm tempted to enter it as #2.  I'm dead certain that #3 is incorrect, but I suppose it could be an option.

I don't know, but I credited B. B. King and His Band as B. / B. / King [B. B. King and His Band].

Looks like that CLT credit is for a French release of the film in question, Sidewalks of London - in which case the credit is likely "Carroll Gibbons and His Orchestra" just as my copy is.  Could be wrong, as there are rare instances of credit differences in different releases, but I doubt it for a film this old.

Thanks for your input, everybody.  Like you pointed out, Skip, I disliked #1 because I couldn't get all the data in.  Since Carroll // Gibbons and His Orchestra fits it all in, I've decided to go that route (especially considering the CLT credit is very likely the same).

I had this with some music DVD's as well, there were different bands credited some of which didn't fit in the first name field.  I choose to use thefirst name till it didn't fit any more, than removed the incomplete word and add that (and the possile rest) to the last name field.

In your example:
1st name fits: Carroll Gibbons and His O 
I'd put in: Carroll Gibbons and His//Orchestra

Paul

As suggested by Kinoniki, I'd go for Carroll // Gibbons.
Not sure if I would use the "credited as" here, I tend to interpret all after the "and" as an additional credit and therefore wouldn't enter "His Orchestra" at all. But this is definitely only a personal preference.