These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Foe Yay: For a time during the 1990s, he dated his political nemesis, Laura Ingraham. Both Keith and Laura have attacked the other on their respective shows ever since. Just which partner would be a Heel would likely depend on your political ideology.
Ho Yay: Olbermann is the most popular subject (along with Jon Stewart) in the world of punditslash.
Crack Fic: Punditslash has a tendency to put him with Anderson Cooper. They don't often interact with each other or bring each other up that much, or hardly ever in fact.
Narm: Frequently. For one example, he made a cheesy analogy about the Skittles that were on him when covering the Trayvon Martin case. There's also the habit of using Godwin.
Older Than They Think: Although Keith was mostly known for doing sports before Countdown, it wasn't his first MSNBC news show. That was The Big Show with Keith Olbermann, which debuted in 1997 after he left SportsCenter ("the big show" was the nickname for the edition of SportsCenter that he co-anchored with Dan Patrick). He left a year later to join Fox Sports Net because he was fed up with the constant coverage of the Monica Lewinsky scandal.
Sending Stuff To Save The Show: An odd variation. Following the announcement of his suspension, several members of the media and a whole bunch of fans came to Keith's defense, most notably an online petition to get him back on the show that got over 250,000 signatures within two days of the announcement. Two days after the announcement, Keith was reinstated. Coincidence?