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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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 make 10+ 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 the witty dialogue and tricky puzzles of previous Monkey Island releases.

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 feel impossible to beat without a guide.

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

Dating show in Leisure Suit Larry 2

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-running Leisure Suit Larry series. 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 Love was 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.

14 Myst

Starting area of Myst

Myst is 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's The Sims.

Myst differentiated 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 to Myst'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.

13 The Hitchhiker's Guide To The Galaxy

Text screen and bedroom

The Hitchhiker's Guide to the Galaxy was initially released all the way back in 1984 and is a text adventure game based 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.

12 Day Of The Tentacle

Day of the Tentacle main characters

Day of the Tentacle is one of the most critically acclaimed point-and-click games of all time, exemplified by the original version's 93 Metascore.

LucasArts' 1993 release stood 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.

11 Discworld 2: Mortality Bytes!

Characters sneaking into the cart park

Discworld 2: Mortality Bytes! (also known as Discworld 2: Missing Presumed...!?) was initially released in November 1996. The game is a sequel to 1995's Discworld, 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 and excellent voice acting.

10 Grim Fandango

Sea-bees talking to Manny

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 Fandango was 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 Fandango is certainly worth playing, especially with the remaster now on Game Pass, though players should be prepared for an excruciating experience at times.

9 Monkey Island 2: LeChuck's Revenge

The infamous monkey wrench puzzle

Monkey Island 2: LeChuck's Revenge was released in 1991 and, like Grim 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 2 suffers 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.

8 The Legend Of Zelda

Link fighting enemies

The original Legend of Zelda is 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 in Breath of the Wild, though it made some of the game's more tricky puzzles extremely tough to solve.

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

Larry about to fall off a platform

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 was Leisure 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.

6 Riven

Round houses from Riven

Riven was released in 1997 and is the sequel to the smash hit puzzle game Myst. The game features very similar gameplay to its critically acclaimed predecessor, which was a divisive decision at 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.

5 Broken Sword: The Shadow Of The Templars

Broken Sword The Shadow of the Templars - character walking down the street

Broken Sword: The Shadow Of The Templars is on this list for a very similar reason as Monkey Island 2: LeChuck's Revenge, in the sense that the game is already challenging enough, but there is one puzzle in particular that drove many players crazy.

That puzzle is known as "The Goat Puzzle" and is so infamous that it has an entire Wikipedia page dedicated to it. The premise of the puzzle is simple; players need to walk past a goat. However, there's one very prominent issue, as the goat will attack the player when they get close to it, making it seem like the solution is elsewhere. In fact, players do need to be attacked by the goat but must interact with some machinery afterward to trap it, something that most players didn't believe was even possible.

4 Castlevania 2: Simon's Quest

Castlevania II Simon's Quest - cover art of protagonist

Castlevania 2: Simon's Quest was originally released in 1987 by Konami and is one of the pioneers of the Metroidvania genre, thanks to its excellent level design and enjoyable combination of platforming and action gameplay.

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Unfortunately, many players ran into some issues with the game's riddles. There are 13 hidden clues in the game that are needed to solve Dracula's riddle, which are tough enough to find and solve in the Japanese version, but extremely difficult elsewhere as the translation's wording isn't clear at times, making some clues misleading for western audiences.

3 Gabriel Knight: Sins Of The Fathers

Character looking at the camera

The final point and click game to feature on this list is Gabriel Knight: Sins of the Fathers. The 1993 game was released by Sierra and performed extremely well with critics, winning numerous end-of-year awards.

Unlike some of the other entries on this list, the game doesn't feature one puzzle in particular that had players reaching for a guide. Instead, the game spread its misery out, providing tons of challenging and obscure puzzles for players to solve across the game's 11-hour runtime, an impressive length for its time.

2 Metroid

2D view of Samus

The first entry into the Metroid series and one of the most iconic Metroidvania titles of all time was initially released in 1986 by Nintendo. The game helped kickstart the Metroidvania genre with its interconnected level design that required players to continuously backtrack after learning new abilities to access previously inaccessible areas. With such a large map for its time, many players were constantly getting lost and needed to use a guide to map out exactly where they were and where they needed to go.

1 StarTropics

Title image for StarTropics

The word "impossible" in the title of this list is, of course, intended to be taken loosely. However, StarTropics is literally impossible for numerous players to complete without a guide due to one particular puzzle.

At one point in the game, players need a code, which they can reveal by dipping a physical piece of paper in water. This piece of paper came with the game, but unfortunately for some, they had either thrown it away or lost it before the puzzle arose. Moreover, the team that ported the game to the Nintendo Switch seemingly didn't know that the puzzle existed, as they didn't offer an alternative solution, so using a guide is literally the only way to solve it.

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