Ollie rips the buttons off his blue shirt as he gets into the costume for the Sweeney Todd skit. After the skit, the buttons are sewn back on and he isn't wearing the white T-shirt underneath.
In the first scene, at the Christmas party, Santa Claus is sitting on the throne in the middle of the room with a girl on his lap. When Ollie walks up there seconds later (in the next shot) they are both gone.
When Ollie Trinke is checking out at the video store, the VHS boxes behind Maya change between shots.
While Gertrude is putting on her earrings during her fight with Ollie, she leaves the room without putting on the left earring; in the next shot of her in the next room, that ear sports an earring.
After their argument, Ollie goes upstairs and sits on Gertie's bed and finds out that she sleeps with her mother's picture. He takes the picture from her hands, and when she wakes up and they speak, he gives the photo back to her twice.
Gertie's gravestone indicated she died (in childbirth) on June 1, yet she was extremely pregnant in the scene where she was preparing to attend the Video Music Awards, which are held in late summer/early fall. Ollie and Gertie should have been preparing for the MTV Movie Awards, or else Gertie delivered about six months overdue.
When Ollie picks up Gertie at school and they are discussing "Cats," as the camera alternates shots between the two, the background noticeably moves at different speeds: slower for Ollie, faster for Gertie.
The scene from the "Sweeney Todd" play shown occurs so late in the play, Sweeney would have already murdered several people, so Ollie should not have been surprised.
When Ollie exits the Holland Tunnel circa 1995, three American flags are suspended over the tunnel entrance. These flags were not put up until after 11 September 2001.
In Ollie's office, there is a poster in the background for Songs: Ohia's "Ghost Tropic" album, released in 2000. The scene takes place before Independence Day (1996) was released in 1996, before Songs: Ohia had even released their debut album.
Equipment is reflected in a window of one of the houses the Batmobile passes as Ollie and Gertie travel home from school in it.
Ollie cautions Gertie to flush the toilet, but never mentions that she should wash her hands after using it. For a protective father like he is, this makes little sense.