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 three 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!

I later came across I Need Someone recorded on Century (thanks Dante Carfagna) which is a far better mix with the horns much further forward and the vocals more clearly articulated.

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).