Jester Rogue Archetype

[Grek]

Pratfall
When you choose this archetype at 3rd level, you gain the ability to shove a creature of any size and to make shoves with a Dexterity (Acrobatics) check in place of the usual Strength (Athletics) check. As a reaction to a creature adjacent to you falling prone, you may inflict your full sneak attack damage on that creature.

Truth to Power
Starting at 3rd level, you may make a Charisma check with advantage once per short rest, so long as that check is made against a character with a better lifestyle than your own, or to benefit a character with a worse lifestyle than your own.

Play Along
When you reach 9th level, you learn that it is often better to run with a joke than to try to spoil the fun. Once per long rest, you may voluntarily fail a saving throw and suffer the consequences for one hour. After the hour is up, you are treated as if you had instead passed the saving throw.

Prankster
When you reach 13th level, you gain advantage on all Dexterity (Sleight of Hand) checks made to plant or switch an object.

Merry Chase
Starting at 17th level, you learn to distract your enemies through amusing cowardice. Whenever you start your turn adjacent to an enemy, that enemy suffers disadvantage on all attacks it makes while not adjacent to you until the start of your next turn.

[Bjarkmundur]

This is amazing in so many levels. I had to google what a pratfall is, which lead me to a youtube video with Kevin and Jimmy from the tonight show. I had a blast xD

I love that you used lifestyles, I think they are definetly an underrepresented aspect of 5e.

I'm not a fan of Play Along, mainly due to its extreme niche, and that it requires you to know what spell is being cast in order to utilize effectively.

May I suggest instead "You can choose to roll the save with a disadvantage. If you do so you gain advantage on the next saving throw you make."

[skaeren]

The Fool <3

[Lil Mordecai]

That's really fun

For merry chase, since they're distracted by you it would make sense that they would have disadvantage against all targets other than you, sort of like a cavalier's challenge. Or, the ability could give you/maybe others advantage, which has synergy with sneak attack damage