So I’m dming a game in early February and I need help. My plan is to get the party at least to the entrance to the boss room in a medium difficulty dungeon in the first campaign.  My problem is this.  I’m haven’t exactly filled up said dungeon with loot.      It would be really easy for me to put +1 weapons and healing potions everywhere, but I’m afraid that would be boring. Should I add Silly/almost useless magic items? Is there a balence between silly magic items and simpler but less interesting items?

For example I talked to one of my PCs about magic items and I told him about The Decanter of Endless Water. He got a kick out of the idea of pressure washing people even though it was mechanically weak. Are there other silly/stupid magic items you would suggest.

Is this a one-off, or are you planning a long campaign with world-building and persistence? My answer would be different in both cases.

If it's a one-off, do whatever zany stuff you want. You'll never use these characters again so who cares? Do what is fun.

If it's a long-running campaign with many connected adventures you plan to run for maybe a year or more, then I would personally recommend against dumping silly magic items on the party that they may have for many adventures. One or two for flavor is fine. A whole bunch of them would become just absurd. Unless, of course, you want to run a "Tom and Jerry cartoon" type of campaign, in which case, even here, the sillier the better.

I’ll probably give about two to four to the party, since it’s a shortish campaign in my head but it might span a few sessions.

bag of beans timed right makes for a possible epic and definitely unpredictable ambush.

I’ll definitely use Cloak Of billowing and The alchemy jug. I’ll be surprised if my PCs don’t find at least one ridiculous way to do something using one of these.
 Also, I may use bag of tricks instead of bag of beans, but I may change my mind.

I want a Cloak of Billowing now....

The DM in one of the campaigns I play in allowed my Bard to have a “special” magic item that combines the Cloak of Billowing and a Cloak of Many Fashions, and I think it’s a ton of fun.

 So just curious looking up when Mayo was invented, and dam, Mayo is a lot older than thought.  

Quote from Jiracorp626 >>

 So just curious looking up when Mayo was invented, and dam, Mayo is a lot older than thought.  

 Lol

Mayo is 20 years older than America. Invented in 1756.  I thought Mayo was invented like maybe 1940s, lol

I gave a player(dragonborn named Reptar) armor of gleaming. After a few sessions I had NPCs start calling him "Reptar the untarnished" I like giving low level players Iconic visible items that I can have NPCs use to recognize the PC's. So armor of gleaming, glowing sword, super ornate bard instruments, ECT.

Heward’s Handy Spice Pouch, Perfume of Bewitching, and Smoldering Armor are also fun.

You should check out how old mustard is.

I made a stupid sword for a bard once - the rapier of embiggening. An otherwise limp rapier that only becomes useful and erect when in combat with a female (or just opposite sex). Surprisingly more useful than expected since when limp it can fit in a backpack. Not so useful if you are sneak attacked by a female however

One of my favorite "silly" items was the Bag of Many Loaves. It bakes fresh bread when it detects a hungry creature within a certain range... Of course, it's hard to sneak up on goblins when the bag detects hungry creatures in the area.

Homebrew has some fun silly items

I think a busted deck of illusions where there’s something wrong with each of the illusions is a fun item

The fun thing about esoteric items is that you can be more liberal with them than you can straight upgrades.  A campaign's Weapons and Armor of Power should be doled out with a fair degree of caution, but almost anything on the 'Common Magic Item' list from Xanathar's, or many of the 'utility'-tagged Uncommon items in the game, are great for dotting more liberally through your game or putting in the hands of NPCs that aren't necessarily campaign bosses, but are more important than nameless grunts. 

Players can have a bunch of these things without really unduly affecting combat balance, and if they occasionally use a 'weak' magic item in a novel and/or hilarious way to circumvent a puzzle or navigation challenge?  That's just part of playing D&D

For extra silliness and creativity check out the minor properties & quirks you can assign magic items on pg 143 of the DMG. Great way to add some personality to simple items. And it gives you a lot of creative licence to play around with.

A bag of holding is awesome, but what about a hat that functions as a bag of holding made by mindflayers that (muttering quirk) sometimes grumbles and mutters. A creature who listens carefully to the item while it is on their head might learn something useful. Maybe it also has the guardian minor property (Guardian. The item whispers warnings to its bearer, granting a +2 bonus to initiative if the bearer isn't incapacitated) as the grumbling voices from the void of the “hat of holding” warn you of danger.

OborLauren’s wonderful Alchemy jug might actually be possessed by the sprit of “Louis the Mithral Chef” after a rival imprisoned him inside it during a cook-off. When it is used you can hear Louis singing his recipes like he used to do around the kitchen while he cooked (Song Craft minor property. Whenever this item is struck or is used to strike a foe, its bearer hears a fragment of an ancient song). Occasionally you also hear Louis drop his pots and pans as he was known to be quite rubenesque and clumsy. This is usually followed by a stream of colourful dwarven curses and yelling (Loud quirk. The item makes a loud noise-such as a clang, a shout, or a resonating gong-when used).

*(Could even add one of the MINOR DETRIMENTAL PROPERTIES on page 220 of the dmg) while In possession of the, Alchemy jug you must eat and drink six times the normal amount each day as hearing Louis describe his food in song makes you mouthwateringly hungry when you eat.) a remove curse spell cast on the jug ends this effect.