A Tale of Two Crosbys

The happy conclusion to one of Hollywood’s darkest stories

5 min readNov 2, 2020


The legendary entertainer (left) and his grandson (photos courtesy of Bing Crosby II / Wikimedia Commons).

So wrap your troubles in dreams
And dream your troubles away

-Bing Crosby, “Wrap Your Troubles in Dreams”

“Addiction,” says the man on the phone, “is rampant. It doesn’t discriminate. No one is immune.”

He pauses. Then adds, with a sigh, “It was pretty rampant in my family.”

The man’s name is Bing Crosby. That’s Bing Crosby II, grandson and namesake of the legendary singer and actor.

The famous Bing and family lived, to judge from the parade of magazine spreads of the day, an idyllic life.

Trimmed trees … steaming cocoa … photograph smiles.

But things are never quite what they seem. Not in Hollywood.

As an up-and-coming young crooner, Bing Crosby overindulged in alcohol. This was no great secret — and no rarity. It was the Roaring Twenties, after all, and gin mills abounded.

A young Bing Crosby (Wikimedia Commons).

With a new decade came changes, and in 1930 Bing made a pair of vows. The first, a vow of marriage, was to singer and actress Wilma Wyatt (aka Dixie Lee). The second was a vow of semi-temperance: to dramatically curb his alcohol consumption. While Bing managed the latter with little difficulty, his young wife, her career waning, herself took up the bottle. Despite the interventions of friends and family, Wilma remained a severe, reclusive alcoholic until her death in 1952.

Wilma Wyatt (Public Domain).

All four of the couple’s sons — Gary, Lindsay, and twins Phillip and Dennis — struggled with addiction. Their frequent brawls, auto-wrecks and arrests attracted more notice than their short-lived Vegas singing act The Crosby Brothers. The publication of Gary’s tell-all memoir Going My Own Way, which alleged serious (and contested) parental abuse, only widened the deepening rift between the brothers.




Author/cartoonist. Contributor: New York Times, Playboy, Wall Street Journal, Saturday Evening Post, Reader’s Digest. https://ko-fi.com/rolliwrites