The Cheyenne Social Club. Henry Fonda and Jimmy Stewart. Directed by Gene Kelly. The ladies of said club include Shirley Jones, Sue Ane Langdon and Elaine Devry. Plus a nice performance by Dabbs Greer. IMHO the best western ever made.
Is the comedy Something Big with Dean Martin definitionally a B-movie? I surprised myself by finding it okayish and I wasn’t usually that big of a Dean Martin fan. I sort of slot it in a lower category of Western just because of Dean Martin 
. But warning - I saw it over 30 years ago, when I may have had lower standards 
.
I once stumbled across this movie late at night on TV. It’s pretty good—Gregory Peck is in his element as “Stretch,” and a very young Anne Baxter is both gorgeous and a great actress.
You might like High Plains Drifter, a high concept western directed by and starring Clint Eastwood, in his attempt to make an American ‘Spaghetti Western’.
A stranger rides into town and is asked to protect the town from some bad guys coming for them, but not all is as it seems… I’m not sure it classifies as a ‘B’ movie, but it was low budget and was made before Eastwood was a huge star.
This is the quintessential Dean Martin comedy Western! I saw it at a drive-in one night in August 1967 and laughed myself silly. It was on a double bill with The Dirty Dozen, which was kind of an odd pairing (to say the least).
“Don’t worry, I’ll find you! After all, Texas isn’t even a state. How big can it be?”
Big Jake. A John Wayne and Maureen O’Hara movie. With Patrick Wayne, Ethan Wayne, Christopher Mitchum, Bruce Cabot as Sam Sharpnose, Richard Boone as the bad guy. The singer, Bobby Vinton plays one of John’s son and he gets shot early, witlch is a plus.
Many thanks for the invitation.
The Ox-Bow Incident (1943) – Anti-lynching western with Hank Fonda.
Bad Men of Tombstone (1949) – No good guys in bleak story of outlaws turning on one another.
The Baron of Arizona (1950) – One of Vin Price’s best roles as late 19th century grifter working the long con to prove he legally owns the entire state.
Johnny Guitar (1954) – Now-classic western pits aging Joan Crawford vs. shrill Mercedes McCambridge as the men in their lives stand around and act confused.
The Beast of Hollow Mountain (1956) – No better than the second greatest western ever made with a (stop motion) dinosaur.
Forty Guns (1957) – U.S. Marshals take on cattle baroness Barbara Stanwyck in stylishly directed, heavily Freudian film featuring one of the longest and most impressive tracking shots ever done.
The Ride Back (1957) – Similar to 3:10 to Yuma, but even more obscure and in some ways better (e.g., some Bergman-like cinematography).
Terror in a Texas Town (1958) – Slow, very low-budget western showcasing eccentric elements, e.g., a gunman with a metal arm, harpoon vs. gun duel, etc.
Walk Like a Dragon (1960) – Unusual racially-tinged story of cowboy Jack Lord buying a Chinese woman with consequences for both.
Any Gun Can Play (1967) – Bounty hunter George Hilton (aping Clint), bandit Gilbert Roland and bank official Edd “Kookie” Byrnes (sans comb and Kookie T) vie for stolen $$$. I think this was actually intended as a parody; in any event, it has some of the best fake-Sergio Leone direction ever.
The Jackals (1967) – Remake of Yellow Sky (1948) can’t match its star power, but ends up more interesting reset in South Africa with Zulus instead of Indians. Vin Price barely hams as miner confronted by outlaws wanting his gold and tomboy granddaughter (Diana Ivarson, outdoing Anne Baxter in the original, imo).
The Valley of Gwangi (1969) – The greatest western ever made.
NOTE: List does not include Canyon Passage (1946), My Darling Clementine (1946), Rancho Notorious (1952), The Good, The Bad and the Ugly (1966), Once Upon a Time in the West (1968), The Wild Bunch (1969) or Blazing Saddles (1974) - seven of the greatest westerns ever made sans dinosaurs - none of which can legitimately be called a ”B western,” imo.
Great non-standard Spaghetti-O western- My Name Is Nobody, with Terence Hill and Henry Fonda.
An off the wall one:
Curse of the Undead – Preacher Dan must save his town from a long, tall vampire that rides in to town with an eye for the ladies. Kinda eerie. Why, yes, there’s a shoot out, I’m glad you asked.
Needed a better title.
I’ll see your Curse of the Undead, Partner, and raise you with Billy the Kid versus Dracula:
This is the absolute bargain-basement comedy Western:
Gilligan’s Island in the Old West. Watch it once, just so you can say you did.
These two are, I think, a bit better:
Glenn Ford is a greatly underappreciated actor, IMO. The Tracy film is a contemporary Western and is very, very good.
I second the vote for Walk Like a Dragon. Mel Torme both sings and acts alongside Jack Lord.
One more that’s pretty good:
Charles Bronson and Toshiro Mifune. Who could ask for more?
Maybe not a Western per se, but this is a damned good movie that’s largely and undeservedly forgotten:
NM, should have read further. 
My two best recommendations. I usually watch both once every year.
Dodge City 1939 directed by Michael Curtiz and starring Errol Flynn, Olivia de Havilland, and Ann Sheridan.
The Virginian 1946 directed by Stuart Gilmore and starring Joel McCrea, Brian Donlevy, Sonny Tufts.
Has one of the more explicit hanging scenes that I’ve seen in movies made under the The Motion Picture Production Code of 1930 (Hays Code ).
The director avoided censorship by showing the feet jerking. Its quite effective and reminds the audience that hanging is a brutal form of punishment.
If you are going that route, you have to watch 4 For Texas.
And despite its star power, this was definitely a “B” western.
Dang it, ninja’d by six hours so I’ll have to firmly second the notion. While the films cited were definitely ‘B’ pictures – The Tall T had a budget of $200,000, not a lot of money even in 1957 – Boetticher could squeeze more out of that budget and get it on the screen better than anyone else in that period.
Low budget films require a special type of director and writer.
The writer has to create small scenes that use a limited number of sets. It’s similiar to the requirements of a stafe play.
I enjoy watching B movies and study how they saved money on sets and a small cast.
Once I saw some mentions of Dean Martin, Four for Texas immediately sprang to mind. Martin, Sinatra, Andress, Ekberg. Plus a special appearance by the 3 Stooges. What else could one want in a western?
I second The Hallelujah Trail. If you can get past the racist depictions of the natives. (Which is going to be a problem with a lot of these films.) It’s the secondary actors that make this film: Donald Pleasence, Brian Keith, Martin Landau, Dub Taylor, etc.
And don’t get me started on Cat Ballou.
Big Jake is a fantastic movie. It brings back Maureen O’Hara and numerous great scenes of the Duke killing people, especially killing the bad guy trying to harm his grandson with a pitchfork.
Dumbass: I thought you were dead!
Big Jake: Not hardly
Shot Gun: BLAM!!!
Technically, no. The “B” partly has to do with being the second feature in a double feature; such movies typically run under 90 minutes, sometimes well under. GBU is nearly double that.
My answer to the OP:
I highly recommend the Terence Hill/Bud Spencer films, They Call me Trinity and Trinity is Still My Name