The Gambler V: Playing for Keeps

• Directed by Jack Bender
• October 2, 1994

Main Cast

• Brady Hawkes-Kenny Rogers
• Butch Cassidy-Scott Paulin
• The Sundance Kid-Brett Cullen
• Etta Place-Mariska Hargitay
• Jeremiah Hawkes-Kris Kamm
• Flatnose Curry-Stephen Bridgewater
• Frank Dimaio-Richard Riehle
• Ford Hayes-Ned Vaughn
• Black Jack-Martin Kove
• Lillie Langtry-Dixie Carter
• Fanny Porter-Loni Anderson
• Lynch-Geoffrey Lewis

When Brady’s son Jeremiah gets mixed up with Butch Cassidy and the Sundance Kid, Brady hunts them to get Jeremiah out of the gang before he is in too deep to avoid the law.

The Gambler V: Playing for Keeps is the final film/miniseries for the character of Brady Hawkes. As sent offs go it’s not bad. It certainly leaves the door open for more but acts as a standalone film to cap the character’s story.

Once again a Gambler film benefits from not having Billy Montana (Bruce Boxleitner) present in much of the story. He shows up in the opener where we learn Brady Hawkes (Kenny Rogers) is trying to become a rancher having won a failed ranch in a card game but beyond that he’s not a factor in the narrative at all leaving Kenny Rogers to carry the majority of the story.

Brady Hawkes becomes framed as a man who realizes that he has more years behind him than head of him. You’re left with a feeling that he looks at the ranch as a way of putting down a legacy and having something left behind to be remembered for. When he learns that his son is riding around with Butch Cassidy he sets out to bring him home. 

In that it is about a father trying to make up for the mistakes of his past. While the story is built around the adventures of the Wild Bunch with plenty of fictional elements, it’s also about Brady finally confronting his past and becoming the father he should have been. Despite paying for his son’s schooling, he’s been an absentee parent. Jeremiah has viewed this as a lack of love from Brady and now these two must form a bond.

As with previous iterations of the Gambler we encounter real Western historical figures. Not an uncommon element for the Western in general. I think it works a touch better here than it did before as what’s happening with him some of them parallels a bit what’s happening with Brady and Jeremiah. They need to make some serious decisions. Should they continue to lead life as they have been which will lead to a dead end or take things more seriously and work to build something of substance? Should they just let life push them along or should they take charge? The fate of Butch and Sundance and the rest of the Wild Bunch are all assured but there’s hope for Brady and his son.

This is not without humor but The Gambler V: Playing for Keeps is much more serious of a film and in tone is what this series always should have had. It’s not soul crushing and it’s not filled with terrible people, but rather it’s more in line with the tone of the song.

Once you realize how heavily connected to the fate of Butch and Sundance, this film is, it takes on a slightly less slightly more down be tone than it already had. You’re not going to walk out this depressed butt because of the focus on mistakes of the past and avoiding a doomed future this film is not as buoyant as the first movie or any of the others here. This is much more serious.

There are also themes of honor and decency and just doing what’s right. While the Pinkerton man who is chasing the Wild Bunch is a dedicated man, he also has a code by which he lives meaning that his jerk employee that’s been a nuisance for Brady eventually gets his just desserts. And rather than sweep everyone up he let go some more harmless individual such as Brady’s son, and the legendary Etta Place (Mariska Hargitay) when they are trying to leave.

Gambling was not as strong a presence here. We get two distinct instances of gambling aside from the off camera bit of getting the ranch. And those were minor. While the card bet between Brady and Jeremiah gets Jeremiah to give him a second chance, it does not feel as if the story hinges in any way on them. This is a film focusing on a gambler and gambling needs to play a large part in it. Or should. The excuse is Brady is concerned he has lost his edge as a gambler and thus is using the ranch as an excuse to not gamble. It would have been appropriate for a subplot to have him proving he clearly had it in the end but that never gets truly highlighted.

Dixie Carter makes what amounts to cameo appearance as the real-life Lillie Langtry who in the Gambler Universe had some kind of relationship with Brady. Dixie Carter was a Southern belle through and through and she could not put on a very good English accent which is a necessity for anybody playing Langtry. Not that she was bad, but her performance was harmed by difficulty with the accent.

Loni Anderson shows up as well known madame Fanny Porter who had a long-standing connection with Butch and Sundance and one with Brady as well. I could see Anderson taking on the part of Langtry and Carter that of Porter for the simple belief that I think Anderson could do the accent so much easier than Carter. At the minimum she could have moved into haughty American which would be close enough.

I am not sure why characters like Burgundy Jones or Kate Muldoon did not make a comeback for even a minor flirtation with Brady. It certainly would have been a plus to grow the central character.

Despite its flaws, The Gambler V: Playing for Keeps is a quality film and it is the type of story I wish this series had started with. Not knocking the others. This is a great more serious Western and it’s a great way to cap off the series. I definitely recommend it!