Bobby, It's Cold Outside

Five weeks before Christmas, Lenny orders his Christmas gift online. Two days later UPS delivers it, but someone immediately steals it.

Working as a lighthouse keeper, Sideshow Bob is visited by Cassandra Patterson, a neighbor. She tells him she mentioned him in town, and Bob knows he let his guard down around her when two men come visiting, but they offer him a job at the Springfield Mall as Santa Claus. Meanwhile, more people are getting robbed of their delivered gifts.

The Simpsons visit Santa's village. Bart skips the line to see Santa, and realizes who he really is. Bob tries to strangle him, but he can't because he refuses to break character.

When a plan to trick the robbers with gunpowder fails for Lenny, Lenny writes 'SB' with his blood. When the news is reported, Homer calls the cops to reveal that SB means Selma Bouvier and she is arrested, freeing the recently-held suspects Scott Bakula, Steve Ballmer, and Sandra Bullock.

Bart still suspects Bob, who agrees to help Bart find the culprit by concealing himself in a box that is placed on the porch.

The thief arrives and the family follows the van to a hangar, finding out Waylon Smithers and Mr. Burns were the culprits. Lisa suggests Burns did it because he's depressed. Mr. Burns tells the story of how as a child he was heartbroken one Christmas, when he asked Santa for just a hug and a smile from his parents and they never delivered, sending him to boarding school instead. Bob as Santa convinces Burns that his harsh upbringing made him the success he is today. Burns and Smithers then return the presents.

On Christmas Day, Homer and Marge snuggle together just before the kids open the presents, and they go to the basement to enjoy some time together, just after Grampa takes a picture to bless everyone with "Merry Christmas from the Simpsons!".

Back at the lighthouse, Cassandra brings Bob a Christmas present, a rake, and tells Bob that she knows who he is. She tells Bob that she wants him to kiss her before the two of them start singing their version of "Baby, It's Cold Outside" together. She and Bob then sign a "Snuggle Contract" saying that both of them knew what they were getting into, just after Captain Horatio McCallister crashes into a rock because the lighthouse light wasn't lit.

At the Springfield International Airport, Ballmer meets Mr. Burns. Burns asks him how he could be so positive about everything and asked if he could teach him how to do it. Ballmer then gives Burns a pep talk. When Burns tries to copy his motions, he hurts himself and has to be taken away in an ambulance, with Steve Ballmer going with him.

Dennis Perkins of The A.V. Club gave this episode a C, stating "'Bobby, It's Cold Outside,' (title referring to one aforementioned credits filler gag) at least sees everyone's favorite ineffective psycho would-be murderer back in town for the holidays. Of all the recurring, non-cast characters, Bob's the one most likely to brighten up my day/any episode, simply due to Kelsey Grammer's obvious joy in the villainous role. (Plus, they always let him sing—put 'Carol Of The Bells' on your Sideshow Bob mix CD.) The never-to-end saga of Robert Underdunk Terwilliger's bloodlust for the blood of one Bart Simpson stretches all the way back to The Simpsons' 12th-ever episode, and he's been swinging and whiffing hard for some 29 years at this point. Like most recurring characters and bits, Bob's appearances have waxed and waned in comic effectiveness, but, hey, always nice to have Grammer in the house, once more essaying his second-most(?) famous role."[2]

Tony Sokol of Den of Geek gave this episode three and a half stars out of five and said "is a double-stuffed bag for the chimney. It is their annual Christmas episode, and these halls are decked. The episode features evergreen favorite recurring villain Sideshow Bob, who trims his tree with ornaments of bleeding Barts. And it bottoms out with our Springfield's favorite Grinch."[3]

• "Bobby, It's Cold Outside" at IMDb