Season 2

After Brad is rude to a fan with autism at a book signing, Jenny McCarthy tells him that he has pissed off the entire autistic community and he has to make a formal apology. Chris goes out on a date finds out that he might be a grandfather. Chelsea wants to buy Jen's friend's dog for 10 grand.

When Sarah gets a glimpse of Brad's penis while walking by as he's changing clothes in his dressing room, things go awry as she tries to prove to Chelsea that Brad's penis is the complete opposite of what Chelsea thinks his entire body is: hopelessly ugly. Meanwhile, Jiffy gets blamed when Chelsea accidentally lets an internal email (insulting Sharon Osbourne) go viral. Chelsea forces Jiffy to take the blame for her mistake, and apologize to the outraged Osbourne in person.

Brad takes Chelsea's differently-abled fan Jordan out on a night on the town to gain points with Chelsea. Heather gets jealous that the talent department takes the free gifts that companies send them to wear. Chelsea tasks Jiffy to deliver a stool sample to her doctor.

Chelsea's assistant asks the group to assemble a "Tribute Book" with photos of them and their mothers for Chelsea's birthday. Chuy invites Brad, Heather and Jiffy to an appearance at a new golf course. Chris and Jen attend Roy's photoshoot for PlayGirl.

The writers struggle to deal with an increasingly lazy and cocky production assistant. Chris feuds with James Van Der Beek over which of them will wear a matching shirt on-air. Josh is dismayed to learn that his son thinks that Chuy is funnier than Josh is.

Heather attends an office party and wakes up with an unexplained hickey; Jen becomes friends with Dave Grohl; Sarah receives a mysterious package at the office.

Reese Witherspoon returns to the Chelsea Lately offices so the writers can help her write a speech she is giving in Chelsea's honor, but she starts to bother Chelsea this time around while earning the staff's praise. Jen lies to Gary of HR to give Sarah a spot in front of the offices, leaving Brad angered that he has to use the parking garage. Roy gets upset when the writers like Chuy's salsa rather than his cooking.

Josh bets Jay Leno over the game at Ross' football party. Chelsea is the only one that enjoys her assistant's character with a lisp. Jiffy meets with Jane Fonda to discuss her coming on the show. Chelsea introduces the group to Jennifer Aniston, who has more to say behind Chelsea's back than expected.