Jon Hamm
Milton Wright - Keep It Up
https://www.youtube.com/watch?v=7Pu7UUNw8RU

But more likely:
Tupac-Keep Ya Head Up
https://www.youtube.com/watch?v=8V0cfqqRYSs

Why? Says he's in "Keeping Up with the Joneses."

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Kate Upton
Passing on this one - that film she's promoting looks like a turn soufflé