Among the multitude of Orthodox Jewish men praying at the Western Wall, one stands out for a number of reasons.
He was born in Central America to an African migrant mother and rose to become one of the biggest rap artists in the United States.
Shyne, as millions of rap fans know him, has also just served nine years in prison for firearms offences, where he rediscovered his Jewish heritage and says he's a reformed man. I met up with him in the Holy City.
Dressed in the smart black outfit of an ultra-orthodox Jew, with a distinctive white kippa or skull-cap, he cuts a cool figure walking through the streets of Jerusalem's Old City.
But for Moshe Ben David this journey is not about style or statements - it is about connecting with Jewish roots which, he says, have always been there.
As he prays at the Western Wall, the Ray-Bans and bling watch are outwardly all that is left of the man he used to be.
Born in Belize, the son of an impoverished Ethiopian Jewish mother, Shyne grew up in Brooklyn where his talents as a rapper were nurtured by Sean Puff Daddy Combs. Writing about the streets, guns, power and girls just as his music career was taking off, the 21-year-old was sentenced to 10 years in jail for his part in a nightclub shooting.
"What am I doing? I'm going to jail for 10 years for what?" says the former bad-boy who's clearly done his fair share of reading and thinking during his time behind bars.
"I'm coming out to show kids that I wouldn't wish prison on my worst enemy. You're better off flipping burgers in McDonald's than going behind that wall, because that wall is hell."
With no hint of irony Shyne says he's now on a global mission and, more than once mentioning Nelson Mandela, says that "prison has been a feature in the lives of many great men".
'Last real rapper'
He is, of course, not the first prisoner to undergo an epiphany in prison but says he's always felt a strong connection to Judaism.
Looking out over the Old City he refutes any suggestions that he is not serious and that his journey to Jerusalem is anything but the real deal.
"I could be anywhere right now - in Paris or Milan, but I'm right here. I've become Hasidic for what? I could have carried on selling records just the way I was," says the rapper after reciting his daily prayers with dozens of other Jewish men underneath Jerusalem's Western Wall.
Later on, he heads off to a Yeshiva or Jewish religious school for several hours to study the Torah - the Jewish bible.
But the 32-year-old reformed bad boy hasn't given up his music - far from it. With two new albums out next year Shyne is, according to one music magazine "the last real rapper still alive", albeit with a new focus in his life.