Here are the most challenging questions Solomon posed to Olbermann, using Comedy Central host Jon Stewart's criticism at the "Rally to Restore Sanity and/or Fear" as a jumping-off point:
At his Rally to Restore Sanity, Jon Stewart complained about the shrieking tone of cable news. Were you watching when a montage juxtaposed footage from your news show with that of Glenn Beck's?
Is it fair to describe you as the first left winger to express anger as a television host? Fury used to be the province of right wingers, until that day in 2006 when you delivered a tirade against Donald Rumsfeld.
Do you think you have an anger-management problem?
Olbermann didn't get the same hostile treatment as the gentlemanly conservative legend Bill Buckley, founder of National Review. Buckley was grilled by Solomon his "many offensive comments over the years" in the July 11, 2004 Times . Here's a sample:
You have made so many offensive comments over the years. Do you regret any of them?
It's not fair to blame the press. Some of your most inflammatory comments have been made in your essays and columns. In the 50's, you famously claimed that whites were culturally superior to African-Americans.
You seem indifferent to suffering. Have you ever suffered yourself?