After completing the Gilded Steam Ship Adventure a popup appears and tells you that you can stay aboard the Gilded Steam Ship or return to the Royal Train Station to continue the adventure. Choose to stay and complete the area. Once you start up, another popup appears, this time explaining Bonus Challenges. Follow the objective marker aft to The Buried Treasure club, where a brief cutscene tells you that the club is now open, and you can begin the “Get the Gits a Gig” Challenge.
Assuming you used my guide to complete that level, start following from here to reach the next achievement.
First, stack into one of the two hillbilly-looking dolls standing just outside of the club. It doesn't matter which one.
Collection: Bobby Webb (25)
Collection: Billy Webb (26)
Then stack into any fancy looking doll and enter the club. The other Webb boy will follow you in. Once inside, stack out of the fancy doll and go up onto the stage.
Challenge: Get the Gits a Gig (1/3) – Fancy Facade
Stack into a Webb boy again and return to the Artistic Makeover shop. Get each of the Webb boys a makeover. You should now have at least 3 of the 5 makeovers required for the “Masquerade Ball” Hi-Jinks challenge. Now simply go into The Buried Treasure club and climb onstage.
Challenge: Get the Gits a Gig (2/3) – Painted Black and White
Stack into Hand and “Toss Cookies” next to the Pirate, causing his parrot to move off of his shoulder. Now stack into one of the Webb boys and then into the Pirate.
Collection: Pirate Chuck (21)
Take a moment to use Pirate Chuck’s “YAR!” ability on dolls to make them faint.
Hi-Jinks: Broadsides! – Use Pirate Chuck to make dolls faint (5)
Once you have done that, go to the door to The Buried Treasure club and “YAR!” the bouncer at the door. Note that this does not seem to count for the “Broadsides!” Hi-Jinks challenge, which is why we did that first. Once inside of the club stack out of Pirate Chuck and go onstage one last time.
Challenge: Get the Gits a Gig (3/3) – Polly Got a Cracker