College of the High Roller

High Roller Bards don’t play taverns or open mics. They play private lounges, roped-off stages, and glittering backrooms with no guest list—just connections. Their magic weaves through velvet drapes and low-lit spotlights, captivating audiences one high-stakes show at a time.

These bards aren’t just performers—they’re event orchestrators, memory shapers, and emotional manipulators, often working with a handpicked entourage of managers, bouncers, and assistants. Or, in true diva fashion, managing it all themselves.

Whether gracing a casino’s top floor, a noble’s birthday gala, or an underworld club known only by password, High Roller Bards are masters of tailoring their show—and its aftereffects—to every room. And when the show ends? No one forgets it. Not entirely, anyway.

Stacked Deck

Starting at 3rd level, your time has been well spent hosting private performances for the city’s wealthy, elusive or global Celebrities. 

• You gain proficiency in two Gaming Sets of your choice.
• You learn two languages of your choice. 
• You gain proficiency in a skill of your choice. 
• You gain proficiency in a toolkit of your choice. 
• You gain proficiency in a Musical Instrument of your choice.

Spot the bluff

When you join the College of High Rollers, at 3rd level, you harness your silver tongue and gambler’s wit to size up the competition and twist their fortunes. During any encounter,

You can use a bonus action to learn if a creature’s Charisma score is higher, lower, or equal to yours and when you expend a Bardic Inspiration die, you can roll it twice. You choose which result to give the target.

OR

You may instead offer a bardic inspiration die to a hostile creature within 60 feet. If they accept, they must immediately roll the die and subtract the result from their next attack roll or saving throw. If they roll, the house takes its cut—you regain that Bardic Inspiration. 

Raising the Stakes

At 6th level, your performances uplift your allies like a well-oiled show team. Choose one of the following bonus effects whenever you grant Bardic Inspiration (you may change the effect each time you inspire):

• Hype Crew: One ally also gains temporary hit points equal to the number rolled on the Bardic Inspiration die.
• Spotlight: One ally can roll the Bardic Inspiration die twice and keep the higher result.
• Stage Partner: When an ally uses the  Bardic Inspiration die, they may also move up to 10 feet without provoking opportunity attacks.

You can use this feature a number of times equal to your proficiency bonus per long rest.

Master of Odds

Upon reaching 14th level, you have learned how to tilt fate itself, nudging every roll like dice under your fingertips.

• Loaded Dice. When a creature you can see within 30 feet makes an attack roll, saving throw, or ability check, you can roll a Bardic Inspiration die and add or subtract the result from their roll after you see it but before the outcome is decided.
• Control the Cards. Once per long rest, when you or a creature within 30 feet rolls a d20, you may declare the roll a critical success (20) or a critical failure (1).