Awesome: Countdown with Keith Olbermann
- In general, his Special Comments.
- His impassioned special comment in defense of LGBT Civil Rights in the wake of Proposition 8, which earned him a GLAAD award. Also doubles as a Crowning Moment of Heartwarming.
- May 2008: During a slam at Hilary Clinton for bringing up Bobby Kennedy's assassination during a campaign speech, watch what happens at 1:37. Crowning Moment Of Badass, anyone?
- September 2008: During the 2008 Republican national convention, Keith lambasts the Republicans for frequently taking advantage of September 11th imagery in their platform.
- January 20, 2009: Finishing his show with his usual X Days Since signoff. "You thought that would change? Are the troops home yet?"
- May 15, 2009: Texas governor Rick Perry wants to secede Texas from the rest of the Union, so Keith blasts him with a metric ton of logic.
- Calling Pat Robertson and Rush Limbaugh out for their comments on Haiti:
"Rush Limbaugh and Pat Robertson, your lives are not worth those of the lowest, meanest, poorest victims of those still lying under the rubble of Haiti tonight. You serve no good. You serve no god. You inspire only stupidity and hatred and I would wish you to hell, but knowing how empty your souls must be for you to be able to say such things in a time of such need, I suspect the vacant purposes of the lives you both live now are hell enough already."
- On ESPN, he calls out the rampant misogyny in sports and sports reporting, calls himself out for gendered offenses against Hillary Clinton and Michelle Malkin, and most of all calls out the NFL for punishing players who are caught smoking weed and beating on other players during a game (at least they're well-padded and have helmets) over players who beat their wives/girlfriends.
- He has also called out women in sports who have been accused of domestic violence, like soccer goalie Hope Solo, saying that domestic violence knows no gender.