10. Harry Caray On Weekend Update
Air Date: 10/19/96
Starring: Will Ferrell, Norm MacDonald
Arguably Will Ferrell's best impression, his version of Harry Caray sounds exactly like the Chicago Cubs' legendary announcer (Listen to Caray in this YouTube clip and try to tell the difference). Will even manages to get the kooky head nod down. But the one thing we are most impressed with is Ferrell's ability to hold that double chin throughout the sketch. Seriously, how does he do that? That had to be uncomfortable.
Everything in this bit comes totally natural to Ferrell; this is one of those handful of SNL impressions that could almost pass for the real person. Although the real Caray passed away in 1998, Ferrell managed to pull out a rendition of Harry Caray in 2010 on Letterman.