The Histroy check is arguably the most "unused" skill check.

Share your ideas about how to make this check interesting, funny or, at any rate, worth to spend a proficiency.

My players have to use history checks pretty frequently for recalling things NPCs told them (that they forgot), or to recall something from the world or a culture they are encountering. Religion checks often fall into a similar category...

It may not be the sexiest skill to be proficient in, but depending on the DM it could be extremely important. Plus, if it makes sense in the backstory/background for the character to be a history buff, why not use it to the group's advantage?

I would allow History check to make the party know about the information contained in the Sword Coast Adventure Guide or the monster lore (MM, Volo's guide...)

I use the history check like a culture check. Like say the party is in a dwarven ruin, they can make a history check to see what sort of dwarven area was this, was it a trading post? Or maybe it was a citadel, or a guard checkpoint? And if they roll high enough (i.e. DC 18+) they might even know the name of the Ruins. 

History, you say?

-Background of the area/land they're on

-Relics/trinkets/carvings they come across (origin of people, how old, etc)

-Historical war tactics as reference for current battles (their own use or recognizes enemy tactics)

-Legends passed down via generations

You determine skill worth by how active you make their counterparts (uses) in-game.

I often use them like lie detector tests. An NPC will reference something historical and the players can test this to tell if they're a liar or what kind of slant they might want to put on things. Or you know... racist. 

I use history checks for just that.  History.

The player may recall that the ruins they are standing on were once a dwarf mine or the ruins of a lost city.  I use the check to relay certain information the player might know.  That the mines were once preposterous till they were over taken by a mysterious darkness etc.  Found items might contain the story of the lost sword of (insert hero name) that went missing ages ago and perhaps some information on the powers of said weapon. 

There is a lot information and clues to events that might unfold can be given out with this check. 

I always make my players use History to remember specifics. Like, they might know that that lone tower in town used to be owned by a wizard without any check, but a high history check will tell them that it's Pliny the Wise who lived there for 100 years before he tragically fell off the top to his death, leaving his tower magically locked and only he knew the unlocking word to get back in. And as their rolls get higher they get more and more specifics. So 15 would just be "Pliny the Wise lived here for a long time" whereas 20+ would get the whole story.

My players thankfully seem to like the lore I made for the game, so history checks work well whenever they enter a new place. I give them background information on the place (any noticeable events there, any important societies that lived there, culture of towns etc).

A fun thing I like doing though is that different players will get different lore depending on their race/background. For example, when the players reach a new mountain, the Halfling may recall a myth about a Halfling hero that came from that mountain. The Elf may remember that the mountain was the site of an Elven civil war etc. Not all of the myths may be true, but it encourages multiple players to try their own history checks to see what lore/clues they get and starts some fun banter between the characters as they argue on which myth is "true."

History is actually the most used information skill for me other than Perception. All of my players can make a history check when they hear a slight piece of lore, legend, backstory, or similar knowledge about the world itself to determine if their characters either remember something or if they have learned of it. It depends on the character as to the DC for the check (PS, I like to set DCs at all kinds of numbers as opposed to the base multipliers of 5 because it makes it more dynamic and, similar to how AC works, it makes more sense).

Say the party needs information about an old structure or an outer plane, the High Elf Ranger Outlander would have a DC 14-16 depending on their favorite background and enemies for a check about the fall of a great empire or an old keep in a large forest, but a Dragonborn Wizard Sage would only have a DC of 10-12 depending on their color because they have sought to learn more of the world from their background. On the other hand, a Lightfoot Halfling Rogue Charlatan would have a DC of 17 because they have not strived to find info out about the outer planes or destroyed structures in the area because their life did not require them to. This allows that the appropriate person is more likely to remember/recall the lore behind something, but if the player who would most likely know about it fails the throw and another player who would likely know little succeeds it, they can feel like they are more versed and it can provide a little spice to the player interaction during the moment. They can then with an easy pass of 0-3 above the DC discover that the empire was the Kingdom of Emerald Grooves and was ruled by a large congregation and council of druids almost 500 years ago, but was defeated somehow. With 4-6 above the DC, they could also recall information that the kingdom was defeated by infighting and the corruption that spread from a mysterious black and blue plague that discolored the many trees of the realm. With a 7 or higher, including a natural 20, they can discover that these trees were overspilled from the Nine Layers of Hell and that some have been spotted recently in this area.

I also do this in the other direction. With a 1-3 Below the DC, they can't recall the name of the empire, but they can remember that it was about 500 years old. Anything in this case 4 and below would yield no new information as they would just know that it was an old kingdom and went away along time ago which was given by the lore piece. If they got a natural one they might misremember some information, but this is primarily comical and adds some hilarious moments when they utterly fail that none of my players find embarrassing at all. If they got a natural one, they would think, but not remember as this simulates them trying to fill in information without knowing anything, that there was no kingdom there just a myth and that the old walls magically came out of the ground.

With everyone rolling, I have not yet had all natural ones with a group of 4-6 on History checks, so that ultimate comical idea of having them believe something that is entirely the opposite has not come yet. 

History checks are really a diverse moment for me where I can do what I love almost as much as having my party succeed in a challenge, tell a story.

https://m.youtube.com/watch?v=u5o7apAP7Cc

This video changed my gaming life. History checks went from being obfuscated into non-existence to being a major part of the way I DM.

Barker always looks like he has a massive hangover, but when it comes to DMing advice, he often delivers something innovative and new.

That is a quiet inspirational video. I think I might try to include this, but my players ARE A LITTLE DIFFERENT (Ask me why if you wish). I will use this in certain scenarios, but because of my settings and players it might not occur too often, but it is quite cool. Thanks for the tip.

History checks are used a lot in my game too, actually! The most common use is a noble, I find, working out what they'd know -- so, as someone else said, a 'culture check' as much as anything. Would you know this family name? Who is the best swordsmith in Waterdeep? What would I know from family gossip?

I have a lot of items in my campaign that are historically significant to the world but that the party has no idea about. If they ask about it, I have them do a history check to see if they know anything about it beyond 'this is the thing we were told to get.'