Ray Charles In Playboy's Penthouse (1960)

Frank D'Rone, June Christy and Ray Charles - from this show.

Playboy's Penthouse was a talk show that ran from 1959 to 1960, the very first variety tv show where blacks and whites sat down and chatted as equals. It can also claim the first appearances of Lenny Bruce and many later iconic stars. The show was hosted by Hugh Hefner himself, in a party setting at a Chicago penthouse.
According to the catalog of the Paley Center, (ID: T:24963), musical highlights of this program, that must be from late 1960, included Ray Charles playing piano and singing Georgia On My Mind and Yes, I Know [a corrupt title; see below], a performance by drummer Gene Krupa and his band, and Frank D'Rone singing The Party's Over. Other highlights included appearances by comedian Phyllis Diller, actor Tony Curtis (who played the flute in a brief segment with the Krupa band while one of the Playmates played the drums), and mime Shai K. Ophir, who talked about the art of mime and performed several brief routines, including the various ways that people smoke cigarettes. Possibly - see photo above - June Christy also guested.

I've watched a 7-minute sequence of the show (poor video, but good sound), where Ray Charles performed very good versions of Georgia On My Mind and Hallelujah I Love Her So. For Georgia it's a 'first known live version' (it's also the first video-taped version of Hallelujah, but that song also survives in a 1957 audio taping of a concert at Carnegie Hall that I haven't heard yet).
Ray played with a trio in which I didn't recognize the bass player and the drummer, but the guy playing flute on Georgia, and taking his tenor solo on Hallelujah, was no other than David Fathead Newman.
The photo with D'Rone and Christie, reproduced above, implies that Ray contributed to at least one more performance - it may well have been the show's finale (maybe a rendition of What'd I Say?).

To get a taste, watch this episode from 1960, with the leader of the show and another performance by  Frank D'Rone: