Lounge Singer’s Road to Top Paved With Bad Detentions

EAST BOSTON, Mass. Bobby Santosuosso fiddles nervously with his bow tie as he waits in the wings at the Aborted Take-Off Lounge, a crowded night spot that overlooks Runway 5N at Logan International Airport here. “I gotta keep myself cool,” he says to his manager Lou Valone. “This is gonna be a tough crowd.”

“We coulda had some fun—if you was not a nun!”


The occasion is the release party for Bobby’s first CD—”Sing and Swing It, Sister!”—a collection of tunes based on his ten years at Our Lady of Perpetual Airplane Noise Elementary School. “I know you’re only supposed to go eight, but I was kind of a cut-up,” he says, explaining that he repeated third grade—twice. “Like the joke says—’What’s the three hardest years of a goombah’s life? Third grade.’”

“The Communion of Saints, cherubim with wings—these are a few of my favorite things!”


Bobby’s years staying after school to bang erasers together and wash blackboards gave him time to steep himself in the culture of the Catholic Church, and his debut album is a tribute, as he will say in his opening dedication, “to the women who made me what I am today—a colossal jerk.”

“Bobby was a bad boy, but his singing was worse.”


After a rousing introduction by his manager, Bobby bounds on stage to sing what his record label’s ”promo” man says is the CD’s one sure-fire hit, “We Coulda Had Some Fun (If You Was Not a Nun)”.

The audience consists of Sisters of the Precious Blood who taught, scolded and smacked Bobby until he graduated from high school, and they seem pleased to hear that they have left an impression on the unruly boy who was almost expelled in second grade for trying to knock the habit off of Sister Annette Cecile Marie Jeanne Yvonne, who was named after the Dionne Quintuplets.

Dionne quintuplets: ”Sister borrowed our names and now she won’t give them back!”


“So many depictions of the cloistered life are false and malicious, but that’s not Bobby’s style,” says Sister Mary Clarus, a tough-talking chorus teacher who takes a dim view of students who talk in line during fire drills. “He’s just stupid.”

After Bobby turns the Bert Bachrach standard “I Say a Little Prayer for You” into “I Say a Long Rosary for You,” he launches into an Italian-American version of McNamara’s Band. “Sister Rita, Agnesita, Arimathea, Dolce Vita, getta some pizza!” he sings, and the audience begins to clap along in time. “He really is a good boy,” says Sister Mary Mark Fidrych, a recent transfer from Detroit. “Underneath all that gel or mousse or whatever it is he puts on his hair.”

“You’ve got to kick the habit, sister, of keeping me after school!”


As he wraps up the set he is greeted as he steps down from the stage by Sister Carmelo Anthony who approaches as if to get an autograph, but surprises him as she whips out a metal-edged ruler and brings it crashing down on his microphone hand.

“Jesus Christ, Sister—what did I do?” he asks as he grimaces in pain.

“Your song ‘I’ve Got You Under My Habit’,” she says with a harsh look on her face. “It was full of impure thoughts, words and deeds.”

Available in Kindle format on amazon.com as part of the collection “Fun With Nuns.”

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