From late-March 2014, actor Josh Charles stopped by the set of KO's ESPN2 show, and played the part of the Dan Rydell character from the TV show "Sports Night", with KO by his side! The Rydell character is somewhat based on Keith himself.
http://www.slate.com/blogs/browbeat/2014/03/31/josh_charles_as_dan_rydell_on_olbermann_actor_reads_highlights_in_his_sports.html
Keith flashback: Josh Charles on "Olbermann"
Re: Keith flashback: Josh Charles on "Olbermann"
Also, here is a running analysis of the same show by someone who is a big fan of Aaron Sorkin, who created the "Sports Night" TV show! His reaction to Josh and Keith shaking hands is priceless!
https://youtu.be/bhbm8vrs4Q0

https://youtu.be/bhbm8vrs4Q0
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