The gaming industry has been through many changes over the last few decades. One change that has been more subtle over the years and has divided opinion among gamers is the easing of difficulty.

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Dating show in Leisure Suit Larry 2

Games from the 70s, 80s, and 90s were significantly more difficult than those released today. This was because it was a way of lengthening a game’s runtime at a time when it was difficult to make10+ hour adventures. Although most classic games are beatable with some persistence, there are some that will make players familiar with a few guide writers by the time they’re finished.

Updated on March 8th, 2022, by Jack Pursey:Fans of classic puzzle games have recently received some positive news, as the iconic Monkey Island series is set to make a long-awaited return this year in Return to Monkey Island. Not much is known about the game as things stand, though the expectation is that it will be a nostalgic return to thewitty dialogueandtricky puzzlesof previous Monkey Island releases.

Starting area of Myst

To celebrate the series' return, and because there is no shortage of excruciatingly difficult games from years past, we’ve updated this list to include a few more games that feelimpossible to beat without a guide.

15Leisure Suit Larry Goes Looking For Love (In Several Wrong Places)

Leisure Suit Larry Goes Looking for Love (in Several Wrong Places)was first released in October 1988 and is the second entry in the long-runningLeisure Suit Larryseries. The game kicks off with the protagonist Larry Laffer winning a free vacation in a game show, though he soon finds himself in trouble after being stranded on a tropical island.

Leisure Suit Larry Goes Looking for Lovewas developed by Sierra On-Line, who was known for creating some of the toughest point-and-click games around, as they presumably wanted people to call their helpline that gave players clues or answers for a fee.

Text screen and bedroom

14Myst

Mystis still, to this day, one of the most recognizable puzzle games ever. The game was initially released in 1993 and soon became the best-selling PC game of all time,a title that it held until 2006 when it was overtaken by EA’sThe Sims.

Mystdifferentiated itself from the popular point-and-click games at the time with its minimal dialogue, opting instead to trust that players would work out what they were supposed to do themselves. This was key toMyst’s difficulty as not only are the puzzles tricky enough to solve on their only but working out where to find the puzzles and what order to complete them in is deceivingly challenging too.

Day of the Tentacle main characters

13The Hitchhiker’s Guide To The Galaxy

The Hitchhiker’s Guide to the Galaxywas initially released all the way back in 1984 and is atext adventure gamebased on the iconic book series of the same name.

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The gameplay is very puzzle-heavy and predominantly requires players to find and obtain items for their inventory that will be used to solve puzzles later on – a common style of gameplay at the time. This process may sound fairly straightforward, though players would often find themselves faced with a puzzle that they had missed the required item for, with some puzzles at the end of the game requiring items from the very beginning, forcing some players to restart and lose all their progress.

12Day Of The Tentacle

Day of the Tentacleis one of the most critically acclaimed point-and-click games of all time, exemplified bythe original version’s 93 Metascore.

LucasArts' 1993 releasestood out from the crowded point-and-click genre at the time by putting players in control of three protagonists who are all sent to different time periods early on in the game due to a time machine malfunctioning. The characters being separated from one another is at the core of the game’s difficulty, as the characters often require items from a time period that they aren’t in.

Characters sneaking into the cart park

11Discworld 2: Mortality Bytes!

Discworld 2: Mortality Bytes!(also known asDiscworld 2: Missing Presumed…!?) was initially released in November 1996. The game is a sequel to 1995’sDiscworld, which easily could have featured on this list as well.

Like its predecessor,Discworld 2: Mortality Bytes!is filled with moon logic puzzles that will often have players thinking, “how on earth was I ever supposed to figure that out?” after giving up and seeking out the answer elsewhere. Still, the game was well-received, particularly for its humor andexcellent voice acting.

Sea-bees talking to Manny

10Grim Fandango

The graphic adventure genre was a dominant force in PC gaming in the 90s. The genre offered players memorable experiences led by charismatic characters while challenging them to solve tricky puzzles.Grim Fandangowas released in 1998 and is considered to be the last great point-and-click game of the decade before the genre’s demise.

Although the point and click genre was still able to provide excellent adventures, players were growing tired of the obscure puzzle solutions, which people believed were intentionally hard as a way of selling tie-in guides and helpline services.Grim Fandangois certainly worth playing, especially with the remaster now on Game Pass, though players should be prepared for an excruciating experience at times.

The infamous monkey wrench puzzle

9Monkey Island 2: LeChuck’s Revenge

Monkey Island 2: LeChuck’s Revengewas released in 1991 and, likeGrim Fandango,was developed by graphic adventure experts LucasArts. The game puts players in control of Guybrush Threepwood, one of the 90s' most iconic protagonists.

Like most graphic adventures,Monkey Island 2suffers from ridiculously obscure puzzles. This was especially the case for non-American gamers, who were infamously perplexed by the game’s monkey wrench puzzle. When players come across a screw that needs tightening, they need to hypnotize a monkey and use it as a literal wrench. This puzzle was already tough for Americans, but far harder for people elsewhere, as the term “monkey wrench” isn’t commonly used outside of the US, making the puzzle virtually impossible for many people.

Link fighting enemies

8The Legend Of Zelda

The originalLegend of Zeldais one of the most influential games of all time. Not only did the game revolutionize the action-adventure genre, but it also gave mainstream gaming one of its first true tastes of an open world.

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Thankfully, the game’s open world was well-designed and fun to explore, as many players would be spending a ton of time in its various areas trying to figure out where to go next. The game offered players very little in-game help, which many people enjoyed and were glad to see return inBreath of the Wild, though it made some of the game’s more tricky puzzles extremely tough to solve.

7Leisure Suit Larry 6: Shape Up Or Slip Out!

LucasArts wasn’t the only company releasing numerous well-designed and comedic point-and-click games, as Sierra Entertainment (known as Sierra On-Line at the time) was also consistently developing excellent adventures. One of their leading series wasLeisure Suit Larry,which followed the loveable fool Larry Laffer as he tried and failed to hook up with women.

Leisure Suit Larry 6: Shape Up or Slip Out!sees Larry win a trip to a luxurious spa, where his attempts to find a partner continuously land him in tough, awkward, or even painful situations.

Larry about to fall off a platform

6Riven

Rivenwas released in 1997 and is the sequel to the smash hit puzzle gameMyst.The game features very similar gameplay to its critically acclaimed predecessor, which was a divisive decisionat the time, as some people criticized the game for feeling outdated.

Although the gameplay mechanics are similar, the game significantly ramps up the difficulty from its already challenging predecessor. Players will need to have a notebook handy to solve the game’s puzzles, as many of them are nearly impossible to work out by just using their heads.

Round houses from Riven