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- Staci has to convince a reluctant Michael J. Fox to be shot out of a cannon on the show. Jim Gaffigan does everything in his power to hawk his new energy drink, EnerrJesus, on Nightcap.
- Gwyneth Paltrow surprises everyone by being a serial thief and overall filthy woman, leading to a confrontation with fellow guest, Jim Norton. Jimmy's dog Monty moves into the office, and famous interior decorator Nate Berkus comes to design an office suitable for late night dog royalty.
- Todd uses questionable means to persuade Nightcap guest, Debra Messing, to make a video for him in character as "Grace." Meanwhile, Tim Gunn pops by the studio claiming Jimmy asked him to come in for an impromptu appearance on the show, forcing the staff to juggle Jimmy's wishes with the scheduled guest, a sloth.
- Transgender personality, GiGi Gorgeous, is a guest and Staci has to convince her to go on a date with Jimmy. Ana is pitching her makeup line and wants Stephanie March to be her new spokesmodel, with unpleasant consequences.
- Celebrity publicist, Malik, needs to find a surrogate for her clients Kelly Ripa and Mark Consuelos, and Staci puts Penny up for the job. Sarah Jessica Parker forms an unlikely bond with a member of the Nightcap staff.
- Whoopi Goldberg, unaware of Nightcap lice infestation, sees everyone has dreadlocks and assumes the staff is racist. Booked guest Denis Leary calls in sick, but Staci isn't having it.
- Famed chef, Mario Batali, tries to aide Staci as she struggles through a horrible bout of IBS. George Stephanopoulos schools Penny on ISIS, an organization she is worried is trying to recruit her.
- Everyone on Nightcap is excited to have Jason Biggs on, but it turns out he's changed a lot since last time. Beth Stern brings kittens to promote animal adoption, but one goes missing.
- Jimmy starts a GoFundMe to make a biopic about himself, and Staci's job is to get Nightcap guest, Paul Rudd, to play "Jimmy." Wendy Williams is also on the show and bonds with an unlikely person over her wig collection.
- Staci interviews for an Executive Producer position at Wendy Williams and seriously considers leaving Nightcap. Mariska Hargitay has agreed to be eaten by an anaconda on air, and Todd gets to direct his first shoot starring Rosie Perez-until Joel Schumacher intervenes.