Have you ever heard of a pop singer from the late Sixties named Marilyn Maye? She holds the record for having the most adult contemporary hits without ever having one reach the Billboard Hot 100 - including one from late 1967 called "Step to the Rear," from the Broadway show How Now, Dow Jones, which went all the way to Number Two on the AC charts, but didn't get anywhere near the real Top Forty.
That's kind of sad, isn't it? It's like holding the record for the most homers by a minor leaguer, or being Miss South Dakota. Apparently she was some sort of cabaret-jazz singer, so she probably didn't care too much about having pop hits, although they sure wouldn't have hurt her career any. Miss Maye is still hanging in there, performing in clubs at the age of 80, so maybe that pop hit is still in the offing.
Actually, Marilyn Maye is tied for the record with Beth Nielsen Chapman, who had eight AC hits between 1991 and 2000 without ever making the Hot 100. Chapman is better known as a country songwriter, most notably on Faith Hill's "This Kiss." But by far the most remarkable thing about her is that she got her start in an Alabama rock band called Harmony, which she joined in 1976 after its former singer and guitarist Tommy Shaw left to join Styx.