"Mr. Dieingly Sad" is a tender, pretty song with a mystical ambience.
The lyrics discuss a walk along the beach with a woman whose "mystifying" happiness confounds the singer (Don Ciccone), who calls himself with each chorus "Mr. Dieingly Sad."
It's never explicitly stated, but the feeling is that the couple is either breaking up or the woman simply doesn't share Ciccone's love. In the end, he makes his final plea:
Then the tide rolls up to shore
I whisper low, 'I love you more
More than even you could know'
Adore me do so I could show
I'm so mystifyingly glad
Not Mr. Dieingly Sad
This was written by the group's leader, Don Ciccone, who passed away in 2016 at age 70. Speaking with Goldmine, he explained that the song was inspired by a real relationship, but it was not a love gone bad. He and the girl were in love, but the Vietnam War was raging and Ciccone knew that he would get pulled into it. His sadness is because he knew he would have to leave her.
Ciccone ended up joining the Air Force, where he was a mechanic. In the '70s, he joined Frankie Valli's Four Seasons, and later did time in Tommy James' Shondells.
The title should be "Mr. Dyingly Sad," but the record company released it as "Mr. Dieingly Sad," making many wonder how to pronounce it when they saw it (deign-ly? ding-ly?). "Dyingly" is the correct spelling and is a real word - it means "in a manner of dying."
The Critters specialized in soft rock with rich harmonies. "Mr. Dieingly Sad" was their biggest hit, but they troubled the charts with a few more singles in 1966 and 1967:
"Don't Let The Rain Fall Down On Me" (#39)
"Younger Girl" (#42)
"Bad Misunderstanding" (#55)
"Marryin' Kind Of Love" (#111)
"Little Girl" (#113)
The song was produced by Artie Ripp, who also produced Doris Troy's "Just One Look