Caray, who passed away in 1998, spent the final 16 years of his career covering the Chicago Cubs where he famously predicted that "as sure as God made green apples, some day the Chicago Cubs are going to be in the World Series" despite their long championship drought.
"This is very interesting to me because clearly you've been following baseball, even though you passed away in 1998," Kimmel said to Ferrell after he entered dressed as Caray with white hair and thick glasses.
"1998? Holy cow, I'm dead," Caray responded.
Ferrell, as Caray, then discussed his shock over learning Donald Trump is running for president. "Donny Trump, oh boy. I knew him when he would sneak into the press box and throw Kennedy half-dollar coins at the Dominican players," he said.
"Trump's got those little tiny mitts. He looked like he was flinging silver dinner platters with those things," Ferrell continued.
Ferrell then called a home run Kimmel hit during a celebrity softball game and launched into a rendition of "Take Me Out to the Ballgame."
Ferrell had previously portrayed Caray during his time on Saturday Night Live as part of Weekend Update and his own skit about space.