In 1935 49 year Al and Ruby adopted a baby boy under the name Al Jolson Junior.
Their marriage had its best period while Ruby was a big success in films.
Al's last starring role at Warners was in The Singing Kid (1936) a misguided attempt to update Jolson with catchy swing tunes. The worst thing about the movie though was the tired script. Arguably Jolson was having more success in radio during this period with the Shell Chateau series. In fact for a time in the mid 30s radio was the only work Jolson was doing.
By 1937 Ruby's film career was winding down and they were soon in each other's pockets. The cracks in the marriage began to show increased by Jolson's frustration about the state of his own career, by 1939 breaking point was close at hand.
That year 53 year old Al embarked on more film work at 20th Century Fox as a supporting actor first singing all his old songs (brilliantly) in Rose of Washington Square (1939) then playing E.P. Christy, the minstrel who introduced many Stephen Foster songs in the film biography of the songwriter Swanee River (1939). He also found time to recreate the Kol Nidre scene from The Jazz Singer (1927) in Hollywood Cavalcade (1939).
It was after he completed Swanee River (1939) that Ruby left Al. Weirdly he tried to win her back by including her in the cast of his new Broadway show Hold On To Your Hats (1940) but the divorce was made final in 1940.
Hold On To Your Hats (1940) saw the return of Jolson to Broadway after almost a decade away. The show was only a modest success, talking pictures had really hit live theatre and Al's voice and health weren't great either.
The show closed in mid 1941 and Jolson had a lonely few months until the attack on Pearl Harbour. He was onto the War Department immediately after the news was announced. "Those guys overseas are goin' need some entertaining. Well I entertain better than anyone else. Get me to them."
So a new generation was soon to discover Jolson, they were Al's favourite audience - the servicemen.