Finding Barry Manilow’s Mysterious Grandfather

He did the crime, he did the time, and then he disappeared — again.

Megan Smolenyak
14 min readMar 9, 2021


Harry Pincus mug shots (New York Department of Correction as seen in Walloomsick Review 22)

I should have known better when I decided to write an article about Barry Manilow’s Irish roots. As an Irish American fanilow, I wanted to know which town or city could lay claim to him (shout-out to Limerick!), but that’s not where the real story was — or where 80% of my research effort went. I only made it as far as his grandmother, Anna “Annie” Sheehan, before getting derailed when I accidentally tripped into a retro, true crime tale featuring a central character who disappeared.

When Harry Met Annie

A New York-born child of Irish immigrants, Annie married young, seemingly to escape a floundering household, but it turned out to be a fire-to-the-frying-pan situation. At the age of 16, she wed Harry Pincus, the son of Russian immigrants, at Brooklyn Borough Hall.

Burial of baby Harry Pincus, Montefiore Cemetery

Two months later, their son — also named Harry — was born, and just two weeks later, he died. The young couple buried their first born on Christmas day at a Jewish cemetery.

Somehow, they soldiered on. Their second child, Harold, was born in 1920. He would spend life as an only child, just as his future son — Barry Manilow — would.

About this time, Annie’s husband began venturing from their Brooklyn home. His brothers moved to Pittsfield, Massachusetts where they would establish themselves in the glass and automotive businesses, and he joined them — sort of. Though Pittsfield was his home base, he worked largely as a salesman and was said to have spent long stretches of time on the road. He also had a side hustle that occasionally kept him away from home — one hinted at by this photo of him with a woman believed to be Annie.



Megan Smolenyak

Genealogical adventurer & storyteller who loves solving mysteries! You may not know me, but chances are you’ve seen my work. (www.MeganSmolenyak.com)