I would guess Bennie Cole and His Soul Brothers were active in Milwaukee, WI since both their 45s have addresses from that city. I only know of the two rare singles illustrated here but both are very good indeed and well worth seeking out.
From listening to them the Raynard sounds like it was cut in the 60s, much earlier than the Key. Love You Till I Die is a fine plodding deep ballad with Cole drifting into an impassioned falsetto from time to time. I like the horn chart and the gentle background harmonies too.
I Need Someone (recorded in stereo) is quite similar in construction to his initial offering, again featuring some strong horn lines over which Cole delivers a superior vocal – just love those falsetto screams at the end. Recordings like these from little known sources are highly prized by collectors – and with music like this it's no wonder!
UPDATE ~ Dante Carfagna writes that the Key 45 came out first on Century with a different mix. Cole's Raynard release features vocals by Gregory Davis, who was also in the group Little Gregory & the Concepts. That ensemble also cut a record around the same time:-
Little Gregory & the Concepts “Get Away!/ Look and You’ll See” (Lompri 270)
FURTHER UPDATE ~ I've now manged to find a copy of the Century City 45 (thanks Andy) and Dante is quite right. It is a far better mix of I Need Someone with the horns much further forward and the vocals more clearly articulated.
Thanks as always to Dante Carfagna (see Links) for the extra info.
Thanks to Alan Wheway for the update to the discography.