Kimmel appeared on Ford Nation via a Google+ Hangout while the Ford's were in a studio.
The segment lasted a little over five minutes, and mostly featured banter between the comedian and Doug Ford, the mayor's brother.
The conversation was awkward at times. At one point, Kimmel talked about getting drunk and not remembering his actions. Ford famously said he did not remember using crack in office because he was in a "drunken stupor."
"I've used that excuse one too many times myself," laughed Mayor Ford on the Ford Nation clip.
The last time Kimmel and Ford spoke in a televised interview, there were questions about whether Kimmel was using the mayor as a comedic prop. Kimmel has repeatedly mocked Ford's personal issues in his stand-up routines at the beginning of his show.
When Ford was in Los Angeles, Calif., on Kimmel's show, the late night host suggested Ford had addiction problems and should seek help.
In this appearance, Kimmel continued to take a mocking tone with Ford. Kimmel was wearing the same suit Ford wore when appeared on the Jimmy Kimmel Show. At the time, Kimmel said Ford was dressed like a magician. "When Rob came out to visit, he was wearing a similar outfit. I admired the look and I've been dressing like this regularly now," said Kimmel.
Ford and his brother Doug joked that the Toronto mayor gives so much material to Kimmel's stand-up routine, the comedian should "get his backside up here" to canvas for Ford's re-election.