|First appearance||When Cotton Comes Marching Home|
|Voiced by||Stephen Root|
Topsy Toppington (1929–2004, age 75) was one of the men in Cotton Hill's platoon in World War II. He remained close friends with Cotton until he passed away, which occurred before the episode "Daletech". Topsy left Cotton $10,000 after his death in Death Buys a Timeshare.
Topsy helped Cotton attempt to assassinate Fidel Castro with a poison dart during a baseball game at Yankee Stadium in 1957, but the attempt failed. In Yankee Hankee, Topsy, Cotton, and others plan to take a small boat to Cuba and finally assassinate Castro, but the plan is thwarted by Hank.
In "When Cotton Comes Marching Home", Cotton Hill claims that Topsy strangled Hermann Göring. Göring, a prominent Nazi, actually died in his cell from ingesting cyanide during the Nuremberg Trials. It is believed that a US guard helped him retrieve the cyanide from his personal belongings.
Topsy also plays a part in "When Cotton Comes Marching Home", where he was participating in the Veteran's Day parade. When Cotton snaps at being mistreated and ignored by civilian society, Topsy aids Cotton in getting revenge on all those who wronged him, such as yanking off the toupee of a job interviewer who rejected Cotton and locking Cotton's boss into a bathroom stall. Cotton then realizes while he got even with those who disrespected veterans, he has still made no progress towards caring for his wife Didi Hill or his infant son G.H.. Topsy offers to help, but Cotton declines, saying some things a man must do alone and thanks Sergeant Toppington for his help (one of the few times Cotton did not refer to him as Topsy).
Topsy's trademark move was puffing up his cheeks extremely large, which often made people around him uncomfortable.