- Directed by Dick Lowry
- November 26, 1987
Cast
- Brady Hawkes-Kenny Rogers
- Billy Montana-Bruce Boxleitner
- Pvt. Bob Butler-Marc Alaimo
- Homesteader-Jeff Allin
- Homesteader’s Wife-Ann Gillespie
- Chief Sitting Bull-George American Horse
- Cpl. Catlett-Michael Berryman
- Deborah-Melanie Chartoff
- Iron Dog-Richard Chaves
- Sgt. Grinder-Matt Clark
- Sen. Henry Colton-Charles Durning
- Lucas-Terrence Evans
- Mary Collins-Linda Gray
- Buffalo Bill-Jeffrey Jones
- Gen. Nelson Miles-George Kennedy
- Mrs. Dickey-Sandy Martin
- Denise-Lenora May
- Peabo Kirby-Marvin J. McIntyre
- Tinkerer-Colm Meaney
- Wade Friendly-Marco Rodríguez
- Charles Afraid of Bear-Jimmie F. Skaggs
- James McLaughlin-Dean Stockwell
- Desiree-Brenda Strong
- Monty the Robber-Monty Stuart
Brady Hawkes and Billy Montana join forces to help stop a Native American tribe from going to war with the US government.
I honestly did not know that there were as many Gambler films as there are. Yet here we find ourselves with a THIRD to discuss. Anywho…

Brady Hawkes (Kenny Rogers) and Billy Montana (Bruce Boxleitner) are back once again and apparently they both have forgotten about Brady’s son Jeremiah. That bothers me. Not once was he brought up at all in this movie. He doesn’t need to be a major character or even present in the film, but a mention of your child-a character that REALLY mattered in the first two films-might be warranted.
This time around the story mixes historical fact with historical fiction placing Brady in the middle of growing tensions among the Plains Indians where he must use his connection with a young warrior chief named Iron Dog (Richard Chaves) that he saved years prior in order to bring Chief Sitting Bull (George American Horse) to the table.
There’s also a bit of a mystery involved in the story as to who and why people are stealing cattle meant for local Indians as part of a treaty. It’s not the most complex mystery or well executed mystery, but it is a mystery and they do it with clues that you have to follow-to a point. Some cards are laid on the table while others are not shown at all. A common irritant for me of televised mysteries from the time.
They throw out red herrings here and there. For one they try to build up Gen. Nelson Miles (George Kennedy) as being part of the nefarious plot. Who would believe George Kennedy could do anything evil? Not this guy. Charles Durning is a different story. Never trusted the guy.

Marco Rodríguez was one of those faces from the time that you saw a great deal of (usually as a baddie) but never knew his name. Always good though. Here he plays incidental baddie Wade Friendly. He was criminally underused in the narrative as a sinister hired gun but really did not matter to the story. Part of me thinks the character was added to pad time. I don’t know but the actor was pretty good and was just great to watch.
And that touches on the presence of Billy Montana. Billy is in this a lot to the point it feels like he is in it a little more than Brady. I am thinking The Gambler, Part III: The Legend Continues was intended (at one point anyway) as a handoff film to Billy. After all Billy Montana is a gambler so you could do another Gambler movie, but with a different gambler.
This is equal parts, fun and serious, with the change in tone not feeling unnatural. There are humorous elements as well as moments of seriousness and commentary on the treatment of need American tribes. In that the film tries to be socially conscious with those moments coming off as heavy handed.
This is as much fun, rollicking adventure as it is commentary. It’s well produced and just well directed. This is probably an improvement upon what had been done previously in the series. By this point Rogers had really improved as a performer though he is not up to Bruce Boxleitner’s level.
This is a bit of a throwback to the older style of Western with a little bit of modern sensibility in it. The good guys are ultimately good, and the bad guys are ultimately evil. The characters are occasionally forced into positions they do not want. There are no great messages other than the poor treatment of Native Americans.
Billy Montana is almost a significant to events as Brady Hawkes is. Admittedly Bruce Boxleitner is the better actor of the two, but this is a Gambler film and not the Billy Montana Show. Whatever occurs should be connected to the main character but I was left with the sense of Billy having many of his own side quests going on. Speaking of which…

Weirdly Billy Montana has a bit of a romance with a prostitute named Deborah (Melanie Chartoff). They do not highlight that too much but she most certainly is part of the entertainment in the West. Billy first meets her when she appears to be getting robbed by it is all a ruse to rob him. Was he that hard up?
Personally I was struck by the number of familiar faces of the time. Most played in the Star Trek universe of the time with the two most notable ones being Colm Meaney (Chief O’Brien) and Marc Alaimo (Gul Dukat). Not just them but the list of all the faces I noticed would be quite long. While Alaimo’s part was important to the story, Meaney was a significant yet completely unimportant character. He showed up in scenes and was the focus of the camera but did nothing to move the story. Squat.
Is Kenny Rogers as The Gambler, Part III: The Legend Continues the greatest Western ever made? No but it’s probably among the better of the Gambler films. It’s not a knock against any of the others. You will enjoy yourself and want to visit it again.


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