Kristen Wiig's Saturday Night Live sketch "Home Alone 2" points out a problem with Home Alone 2: Lost In New York’s classic ending and Kevin’s friendship with the Pigeon Lady. In the sketch, Kristen Wiig plays the Home Alone 2 character known as “Pigeon Lady” while Melissa Villaseñor plays Kevin McAllister in a “never before seen” ending to Home Alone 2, the hit sequel to Home Alone. In the movie, Kevin visits the Pigeon Lady and brings her a turtledove ornament as a gift. She sincerely thanks him, and the film ends with Kevin’s dad discovering his $967.43 room service bill at The Plaza. Kevin's dad screams so loud at the five-star hotel that Kevin can hear him from Central Park where the Pigeon Lady spends her time – and that juxtaposition is precisely what the SNL sketch highlights.
In the sketch, the Pigeon Lady (Wiig) tells Kevin (Villaseñor), “It’s hard being homeless, especially during the holidays.” Kevin replies, “Woah, so you sleep here?” The Pigeon Lady answers that she sleeps under a bridge, to which Kevin replies, “Cool.” When Kevin reveals that he has his dad's credit card, the Pigeon Lady asks him for a hotel room of her own - raising a serious critique of Home Alone 2.
Throughout his interactions with the Pigeon Lady, Kevin is completely unaware that he's extremely privileged and out of touch with the reality of Pigeon Lady’s living situation. SNL uses this as their inspiration for a pointedly hilarious (and gory) sketch. The sketch draws attention to the fact that Kevin has had his dad’s credit card for the entire film (using it to buy buckets of ice cream and rent Angels With Filthy Souls). In Home Alone 2, the Pigeon Lady reveals her tragic past: she was in a committed (likely abusive) relationship and was either kicked out or ran away. Now, people avoid her on the street. Kevin tries to relate to her with a story about his rollerblades and his experience being overlooked as the youngest in his family, to which the Pigeon Lady simply nods and smiles, brushing off Kevin’s insensitivity.
Home Alone 2 tries to communicate that Kevin is just a kid telling innocent stories to the pigeon lady, but both films went to great lengths to show that Kevin – the trap-laying nightmare of Harry and Marv – is wise beyond his years. Kevin is an astute kid who had a mature and heartfelt conversation with Old Man Marley in the first Home Alone film, telling Marley that he should make amends with his son. Home Alone 2 likely tried to recreate Kevin and Marley’s pivotal interaction by creating the Pigeon Lady, but it ends up making Kevin look a bit ignorant. Marley’s problem with his son is relevant to Kevin’s own struggle with his family, but Kevin has trouble sincerely relating to a homeless woman since he’s grown up in a massive suburban home and never wanted for material things.
The details of Pigeon Lady’s life are hidden in the subtext of her conversation with Kevin, so it’s understandable that Kevin might not realize how dark her past truly is. However, even if Kevin didn’t pick up on the details of her life, he would have known that she was homeless. Yet, he didn’t buy her a hot meal or offer to take her shopping for anything she might need. He even told her, “You just need an outfit that doesn’t have pigeon poop on it,” without realizing that she probably doesn't have a choice. SNL takes the Christmas classic, Home Alone 2: Lost in New York and, in an absurd way, points out kind of a serious problem with Kevin and the Pigeon Lady: Kevin spent $900 on ice cream sundaes for himself at The Plaza Hotel, but he didn’t even buy Pigeon Lady a pizza.