Comedy in video games is a tricky endeavor. The medium is ripe for hilarious gameplay moments, but it gets significantly harder when the writers try their hand at cracking jokes with the characters. The following list will detail five games that will tickle your funny bone to no end, and five that try way too hard and fall mostly flat.

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The latter aren't necessarily snoozers all the way through - some of them are quite funny in different ways - but great comedy knows when to not force their humor down the audience's throat. While games still have a problem being funny, they get better at it with the passing years.

10 Tries Too Hard: Borderlands

The Borderlands franchise gets its hooks in gamers with its addictive loop of collecting progressively fancier loot with friends either on a couch or over the Internet. Where it fails, however, is in its writing. The world is a darkly comedic landscape where morbid topics like murder, torture, and corporate exploitation are treated with a light comedic flair. Every character is a psychopath who enjoys killing like they are long Sunday walks on a beach. When jokes work, they simply fade into the background among the thousands of moan-inducing punchlines. It would have worked better if more grounded personalities existed to contrast with the zaniness. Lilith is really the only character who acts like a human being.

9 Actually Funny: Monkey Island

tales of Monkey Island

LucasArts adventure games were the kings of the genre. Not only were they compelling puzzle-adventure titles, but the writing was top notch. The first two Monkey Island titles are all-time classics with the ability to make gamers fall from their seat in laughter to this day. Modern gaming sensibilities make the titles harder than ever, but it is worth it to hear Guybrush Threepwood's inane observations about everything around him. Given his incompetence, it is a miracle he manages to survive all the dangers before him.

8 Tries Too Hard: Eat Lead: The Return Of Matt Hazard

eat lead return of Matt hazard

Eat Lead: The Return of Matt Hazard follows a washed-up video game character trying to make a comeback. The jokes all revolve around video game tropes and stereotypes. Unfortunately, the gameplay is marred by tank-like movement and wonky aiming. The jokes don't exactly inspire one to continue through the journey either. The array of references and allusions are cute at first but grow tiring after just a couple of hours, and they don't let up until the end.

7 Actually Funny: The Outer Worlds

In an age where RPGs are getting bigger and more ambitious, The Outer Worlds came along as a more bite-sized alternative. What it lacks in size it makes up for in the variety of narrative paths and its environmental humor. It is also not a small game by any stretch of the word, with an average playthrough still taking around thirty-hours. Unlike Borderlands, the humor feels less cartoonish and appropriate to the surrounding world.

6 Tries Too Hard: Postal

Many of the best comedians push the envelope of what is acceptable to say and talk about. Many confuse this with humor simply consisting of saying offensive things. Postal is the ultimate purveyor of bad taste. The three titles are chock full of offensive jokes most teenagers would even find too low brow. The gameplay is also terrible, so there is no reason to ever touch this trilogy. If one wants something with a lot of potty humor, it is better to stick to Duke Nukem.

5 Actually Funny: TimeSplitters

The first two games in the series lacked a story, but the humor stemmed from the impressive cast of characters brimming with personality. The third game added a complicated time travel plot following Sgt. Cortez as he jumps through the years tracking down Dr. Jacob Crow. Cortez, despite his combat prowess, is a lovable dork who tries to get his catchphrase, it's time to split, off the ground.

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Additionally, each of the characters he encounters along the way contributes some sort of humor, either as the straight-man or as an even more bombastic personality. Those who played it will never forget the likes of Harry Tipper, Jo Beth Casey, and R-110.

4 Tries Too Hard: Grand Theft Auto V

GTA ferris wheel sunset

The characters in Grand Theft Auto V are fantastic personalities who all go through their own arc throughout the epic story. The cutscenes are all expertly crafted, like they were filming the next blockbuster crime caper. Where the humor falls flat is in the world and the way it develops. Its idea of satirizing American culture is to simply give things different names and hyperbolize its worst facets without actually saying anything about it. Many of these grow tiring as the player spends more time in the world and constantly sees them.

3 Actually Funny: South Park

South Park

Obsidian's two South Park titles prove good adaptations of popular media properties cannot only be good, but exceptional. The small-scale RPGs serve as a perfect backdrop for the series trademark juvenile humor.

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The first game, The Stick of Truth, serves as almost a greatest hits compilation of the best jokes throughout the show's impressive run. The following title, The Fractured But Whole, has more original humor and tells a more unique story. Both end up feeling like a lost season of the show, with the humor and personality to back it up.

2 Tries Too Hard: Saint's Row

saints row 4 president

As inane as GTA V can get, Saint's Row 3 and 4 make the craziest situations of Los Santos look like a grounded drama. It arguably becomes too much, however, feeling like zany for zaniness's sake rather than actually having any substance behind the ridiculousness. With all this being said, the games are still hosts to some excellent moments and missions, like parachuting onto a building while Kanye West's "Power" plays in the background.

1 Actually Funny: Portal

The unique puzzle game packaged within The Orange Box took the gaming world by storm. The only speaking character in the game is Glados, an A.I. who spends most of the game guiding the player through the test chambers while intermittently giving out tidbits about the science facility. Her morbid sense of humor is topped off by the iconic closing tune written by Jonathan Coulton. The sequel ups the ante in every conceivable way with more characters, more puzzles, and even more bizarre laughs. A third will probably never come, but the first two games will make anybody laugh until the end of time.

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