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Bill partied HARD. He was always out wilding and having fun. He still danced & he still went to church because his sister was in NY
Anyway, one day, bailey was at choir rehearsal with his lil sister, who wanted to be famous too. He said she wasn’t talented enough & made her go home. She was like: “I’ll show him.”
Her choir director told her a talent show at an up & coming theater in Harlem
- The Apollo
She entered and WON IT.
And since she went to church and her brother hung out with the New Negroes she was welcomed in and became a big star too. Even bigger than her brother!
She was doing movies! She was on the road with Duke Ellington & Lena Horne. She even did movies
But because they were big individual stars, they never got together much. And after WWII, a lot of work dried up. MGM wasn’t making big musicals, so everyone basically hit the road.
Then they got the opportunity of a lifetime!
Someone wanted to put the old band back together.
In 1949, MGM announced they were going to make a Bojangles Robinson biopic! The old crew agreed to be in it. They canceled tours & got the NAACP’s approval for the script. It was a done deal.
Since Bojangles had died, there was only one person who could play him
Bill Bailey.
So they contacted Bill, who was in NY, and guess what Bill said?
“Nah, I got the Holy Ghost now.”
Ninja WHAT?
No one believed him. Ol hard-partying Bill? They literally just needed him to backslide one more time.
So they got his sister to come talk to him. & he made a deal
“Tell’em to come see me preach. They’ll believe me then.”
Bruh, that dude preached his ASS off.
MGM made “Bojangles” 50 later, with Gregory Hines.
Bill’s sister hadn’t canceled her shows in NY though. She knew her brother loved church.Image
So of course all the legends came by her gigs & hung out with Bill’s little sister Pearl Bailey while they were in town.
And of course, if all those Black musical legends were in town, you know all the white stars were gonna come through. It was kind of a thing
Now this was 1949 at a white club in Greenwich Village. Literally every famous Black musician was in town that week & could fall through on any given night. But Pearl wanted to make her show “diverse.”
So she hired a white opener, probably the least famous musician in the place
So when Bob Hope asked who her opening act was, bc he wanted someone to take on the road, Pearl Bailey was like
“Some local kid named Tony Bennett. You like him?”
The rest is history.
Now here is the moral of the story :
Just because Tony Bennett was a diversity hire who got his job through affirmative action…
It doesn’t mean he wasn’t qualified.