From Indian Territory to the Silver Screen

Reformed Outlaws, the mafia, and the silver screen

It’s safe to say that a career as an outlaw doesn’t lend itself to a long life. Billy the Kid was only twenty-one years old when he was killed. Cherokee Bill a year younger and the notorious Bloody Bill Anderson not yet twenty-five. Jesse James, Joaquin Murrieta, Rube Burrow, Bill Longley, the list goes on.

Not a one of them over the age of forty.

But of course, there are exceptions. Not ALL of the west’s most dangerous men died young. Nor did they simply disappear at the turn of the 20th century. Some of ‘em stuck around and tried to adapt. And I will never NOT find such stories fascinating.

Al Jennings, for instance.

If you’re not familiar, Jennings was a lawyer turned somewhat ineffective bandit. He and his gang operated out of Indian territory and robbed everything from trains to general stores to post offices.

Eventually Al was wounded by law enforcement, arrested, tried, and sentenced to life in prison. Luckily for him, he’d end up getting set free after a couple years due to technicalities and in 1904 received a Presidential Pardon from Theodore Roosevelt (ole Teddy loved his old west guys).

Here’s the interesting part. Al Jennings would live all the way till 1961! This guy’s life spanned from the wild west and robbing trains in Indian Territory to damn near the beginning of the Vietnam War!

Later in life, the reformed Jennings became an advisor for the movie industry and even starred in a few silent films himself.

Here’s Jennings in his 90’s showing actor Hugh O’Brian how to properly hold a six shooter. The police were called in after a concerned neighbor thought the actor was being robbed!

I gotta imagine using some of these real life old west figures lent a little bit of credibility to the movies. We see the same thing even nowadays, only with gangsters.

You ever seen Casino? Remember the mysterious white haired older gentleman that appeared on screen several times as one of Joe Pesci’s henchmen?

You can see him during this mash up. He’s the one that walks up behind the guy in the parking lot at the 1:30 mark and fills him full of lead.

Well, that white haired old man was Frank Cullota, a real life enforcer for the Chicago Mob and member of Anthony Spilotro’s (Pesci’s character) Hole in the Wall Gang. The man was a legit killer and he was simply showing the actors how to properly “whack”someone when Scorsese gave him the role.

When you watch Frank Cullota pretend to kill someone on the silver screen, he’s doing so in a very realistic manner, the same way he did to God only knows how many poor souls during his time as a criminal.

Likewise with Al Jennings. He would have been able to tell the actors how to properly handle a firearm, how to realistically sit a saddle, what it felt like when the bullets whizzed past - how it felt to constantly be on the run.

That said, Al Jennings was also said to not be able to hit the broad side of a barn with a pistol, so who knows.