This was a singing group behind Joe "Fingers" Carr's release in the early 50's.
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the song that Mr Cartright sang was sail away
Sorry not sure about a song called Mr. Winslow in the 90s but there was a song called Mr. Wendel by Arrested Development. I bet that is the one in which you are referring.
The beegees. The song is called lonely nights.
If you're thinking of the song about The Devil and Mr Chips, than that would be 'Chips' by The Real McKenzies.
The Veils sings "Vicious Traditions." An excellent movie.