- Keith's utter SCHOOLING of New York City mayor Michael Bloomberg handling of the OWS protest would have been strictly a Tearjerker or Crowning Moment of Awesome until he got to this line-
- "I'm endorsing you for a fourth term! Your nation needs you, mister mayor! Occupy NEEDS YOU! Bloomberg now, Bloomberg tomorrow, Bloomberg forever!"
- Keith hamming it up in his reenactment of the "Don't Call Me Liz!" e-mails.
- April 15, 2009: Keith recaps the Teabagging Parties.
- Ben Affleck's parody of Keith on Saturday Night Live, for which Olbermann said in a year in review special in 2008 "[I] Hope you got another $7.5 million for that."
- 23-6's clipreel of catchphrases from Special Comments.
- Keith's joy that the new UK government included a man called Ed Balls and he could therefore use the word as much as he liked without repercussions.
- Obama is a secret Muslim, with obligatory Keith ham.
- Accusing George W. Bush of being Muslim. That is all.
- In response to Countdown making numerous references to Rush Limbaugh, Rush came on and challenged MSNBC to not mention him for 30 days. Olbermann responded with "F you!" and for a while had a bouncing "Limbaugh Logo" just above the MSNBC logo in the corner whenever a story focused on Rush Limbaugh.
- November 2010: During the election coverage, Chris Mathews commented that Congresswoman Michele Bachmann appeared "hypnotized" by the crowd behind her due to not directly answering any of his questions. In response, Olbermann quickly began expecting the involvement of The Hypnotoad.
- Keith Olbermann's mockery of Fox News host Glenn Beck is long, storied, and legendary. But this deconstruction of some of the most ridiculous Insane Troll Logic ever heard takes the prize.But do go on - the psychiatrists in the audience are all saying "This is fascinating. Let me grab a prescription pad."Wait, there's weed over there?! I've been coming here for 30 years, and I never knew there was weed over here!So, it's Mussolini and it's Obama and it was carved into the side of this communist building that I work in thirty years before Obama was even born. Yeeeah.
- Keith's reaction to Sarah Palin's turkey pardon video (which happened while other turkeys were being slaughtered in the background).
- On his ESPN show, he made President Obama his Worst Person after Obama said he'd like to host SportsCenter after he left office.So let me get this straight, pal. You've got a job in politics, and you're going to leave that job in politics to go host something on ESPN? (beat) QUIT WORKING MY SIDE OF THE STREET!
- Keith noting that his mother was the real baseball fan in the family. Why is this funny? It's because his dad still hadn't forgiven the Yankees for trading away his favorite player — in 1948. And now we know where Keith gets his ability to hold grudges!
- On his GQ webshow The Closer with Keith Olbermann, his reaction to a poll that said that 31% of people who identified as Trump supporters were in favour of a wall being built along the Atlantic coast of the USA to keep Muslims from entering the country:How are...how are they...I can barely say this. How are they supposedly breaching our present Atlantic fortifications? Rowboating in from Syria, are they? Swimming from the ISIS-infected district of Molenbeek in Brussels straight through to Myrtle Beach, South Carolina?
- Again on The Closer, he quoted a remark by Fox News pundit Sean Hannity: "Now, my overpaid friends in the media, they have their chauffeur-driven limousines", etc.
Funny / Countdown with Keith Olbermann