I believe the men are older in the second photo; hubby says the photos were taken the same day because of their suits. I insist the first photo of the trio is them in their hey-day, playing the college & club circuit; the latter them on the way down, older musicians trying to get a gig -- the same suits are the result of not being able to afford new suits.
A little research shows very little on the trio, other than they were Dorsey, Flo & Jimmy Clark (Dorsey presumably the one, in both photos, with the "D" hanky in his pocket) and they cut at least one comedy/party album. As the title of the recording is The Two Sides of the Nock-A-Bouts, I'm guessing hubby is right. And now I'll need to eat my own hat. Or pith helmet. Or whatever.