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When is it appropriate to use "was" (or the singular form of a verb) when two subjects are grouped? Would the usage of the singular imply the subject is "the relationship of those two subjects"

E.g. Key and Peele was/were funny. (An established group)

E.g. Jim and Pam was/were the best part of The Office. (a specific pairing often used together)

E.g. Chewbecca and the Porgs was/were entertaining in The Last Jedi. (In this case does was have a different meaning than were?)

E.g. Jack and Jill was/were running.

My "intuition" is that was is appropriate in the first three cases, while it's obviously not appropriate in the last one, but I can't determine why it would be appropriate in the middle two.

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None of your example sentences should use was.

The only time when the singular should be used with an X and Y subject is when the subject is a collective singular rather than the conjunction of two separate subjects.

For example:

The fish and chips I ate was good.
Porgy and Bess was written by George Gershwin.
Key & Peele was a comedy television series.
Penn & Teller is a comedy act.

But:

The fish and side of chips I ate were good.
Porgy and Bess were opposed by Crown and Sportin' Life.
Key and Peele were stars of a TV show.
Penn and Teller are comedians.

However, you can also change the subject in the sentence from two conjoined plurals to a singular:

Chewbacca and the Porgs were entertaining.
The interaction of Chewbacca and the Porgs was entertaining.

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