The Marvelous Mrs. Maisel loves to mix the real-life New York City of the 1950s and 1960s (the Stage Deli, the downtown comedy scene, protests in Washington Square Park) with fiction, and though Lenny Bruce (played by Luke Kirby on the show) was a real comic with real arrests and an affection for profane, over-the-top sets, another character, Shy Baldwin, isn't so real. The singer who is giving Midge Maisel her big break didn't exist in real life.
"He's kind of an amalgamation of a lot of different figures who were that successful, but Johnny Mathis comes to mind," confirmed star Rachel Brosnahan when she spoke to Refinery29 at the Maisel junket. There were plenty of performers like Shy, like Sammy Davis, Jr., Nat King Cole, Perry Como, Bobby Darin, and of course, Mathis, who Brosnahan mentioned.
There’s also a good chance that Shy is at least based a little on singer Harry Belafonte, due to two big clues — when Shy and Midge meet at the telethon, Shy tells her that he always hires a comic to open for him. For his last tour, it was Moms Mabley, who was a real comic, and Moms Mabley worked with Harry Belafonte. Midge also tells Shy that her mother secretly loves his Christmas album, and Belafonte’s Christmas album, To Wish You A Merry Christmas, came out in 1958, aka right before this conversation happened. Mathis was also quite well known for his Christmas albums.
Miriam got the biggest break of her life at the end of The Marvelous Mrs. Maisel season 2: Shy called Midge up, just like that, and asked her to be the opening act on his new tour. And, just like that, she said yes. Midge met Shy when they were doing a telethon, he saw her set, he knew she didn’t like Sophie Lennon (Jane Lynch) as much as he didn’t like Sophie Lennon, and that was it. Dreams do come true. This will make or break Midge’s whole career as a comic. But no pressure.
Real person or not, I’m looking forward to seeing more of Shy in season 3, because Leroy McClain, the English actor who plays Shy, has Broadway, TV, and film experience. This guy is a triple threat, and yes, that really was McClain singing in the telethon episode of season 2. I mean, even Midge's mom loves him, and she doesn’t like anyone. And Sterling K. Brown appears in season 3 as Shy’s manager, so who needs a real life counterpart, anyway?