- Crowning Moment of Funny - Quite often in the first 4 games. Almost entirely subverted in game 5.
- The female bandit's valley girl speech in 4 includes a long rant about going to the hootenanny. It's unbelievably funny because her dialog is about a century ahead of the setting.
- Evil Is Sexy - The female bandits in 3 and 4. Possibly 1 and 2, of course YMMV on that.
- Possibly the female gunslingers in 2 and 3. They aren't evil by the plot standards but they do work and kill for money, so...
- Hilarious in Hindsight: If one took Anne Turner from Westward IV and replaced her job at a train station with a job on an apple farm, she'd be practically a human version of Applejack, down to a very similar southern accent, attitude and cowboy hat. Westward IV predates that series by several years.
- They Changed It, Now It Sucks - The original Westward was done in a purely 2D format with an overhead view. When the second game was announced, it was shown to use a fully 3D engine with an isometric view. The game was also redesigned with an experience and quest system used to unlock buildings and upgrades. A town happiness system was introduced which could either help or harm the town. The main setup also featured the Hero character, a selectable main character that didn't need a home and served as a cross between citizens and gunslingers. While this trope was mostly averted in the long run, the initial reaction to the sequel change was surprising.
- Westward Kingdoms may also apply as it completely shifted everything to a medieval setting with a new art style. Much of the humor seemed to be removed and the music felt less cheerful.
- Uncanny Valley - some of the 3D models starting with game 2. They're all fairly simplified to start with but many have these odd, unsettling smiles on them. It's just creepy.