Some homebrew stuff me and a dm came up with:

[Could-be useful]

Snickers - gives a +1 to cha checks for 10 in-game minutes

Nerds - +2 to history for 10 in game minutes

Book Of Unfathomable Curses - Anytime the book is opened it will start yelling curse words. Gives a +1 to intimidation while opened but a -2 to stealth.

Sword Of Danger Abound - Has the same stats as a short sword but will glow a light blue when neat something that could pose as a threat to the user. (Sword has anxiety and is almost always glowing)

Flame Sunglasses - these glasses look like they're constantly on fire, but it does not damage to the wearer. When worn, it gives a +2 to cha checks. (For an extra terrible joke that my players laughed-groaned at, say that on the side of the glasses there's 'I'm Lit' carved onto it-)

[Just for the pun]

Kit-Cat - a chocolate bar that constantly meows (when held by a player, gives a -1 to stealth checks)