Couldn’t you flavor a Ranger or Gunslinger as “cowboy”?

(Going by Pathfinder/D&D base classes only)  
AJ: Ranger  
Dash: Monk(of a race that can fly)  
Pinkie: Bard  
Rarity: Wizard or Rogue with points in fashion related skills.  
Fluttershy: Druid

Careful with the sword there, AJ.

I wrote up a cowboy class, actually. (Called it the vaquero, ’cause why not.) BAB as rogue, saves as fighter.
 
Had a mount. Normal animal but he was good at training it.
 
Wild empathy, animal affinity, some riding feats and mount feats.
 
Rope tricks like a sir. Lassoing, hogtying.
 
Come fights, he works with his fists (gets IUS), bolas, knives, shortsword (believe me, the Bowie knife qualifies), handaxe, crossbows (including the pistol crossbow, of course – in fact, later he can fast-draw). Can wear leather and hide armor, free to take proficiencies if he wants. Gets Mounted Combat a short ways in, of course.
 

 
Never got a chance to try it in a game, but I thought it’d be pretty cool.

Ranger for AJ, rogue or monk for Dash, druid for Fluttershy, wizard or rogue for Rarity, and bard for Pinkie. Easy.

@And Brother I Hurt People  
I would hope now.

From the first panel, I thought this was going to be a Sword Art Online crossover.