Iosif Kobzon has been called the "Russian Frank Sinatra". A velvety voiced crooner, beloved by women, whose career spanned more than half a century? The comparison makes sense.
The similarities between the two go beyond their singing. Sinatra is well-known for his political connections, especially with JFK. Kobzon? He is pals with Vladimir Putin.
And then there are... mob ties. Much has been written about Sinatra's connections with various mobsters. Despite all of those, Kobzon has him beat. He has (allegedly) been involved in everything from money laundering to arms sales to drug trafficking... sometimes through Jewish charitable organizations.
Of course, there are some differences. Sinatra is dead, Kobzon is still kicking it. Sinatra is obviously goyishe. Kobzon, well...
(Editor's update, August 30, 2018: No longer kicking it.)