Washington Post columnist Dana Milbank reflected Wednesday on his career highs and lows—from suing his high school for editorial control of the student newspaper to regularly finding the absurdity in Washington politics—in an entertaining speech to the Upper School.

Milbank was Sidwell Friends School’s featured National Library Week speaker. Scheduled this year during the week of April 11 and sponsored by the American Library Association, National Library Week celebrates the contributions of libraries and librarians and promotes library use.

At SFS, students’ favorite books and bookmarks were displayed in the Upper School library, and the students were encouraged to successfully complete crossword and jigsaw puzzles for prizes. The US library also held a demotivational poster contest.

During his speech, Milbank regaled the audience with humorous stories about his student newspaper experiences, both in high school and at Yale University, and relayed memorable interviews with the famous and not-so-famous. He also showed a video made during the 2008 election season, where he and other well-known journalists spoofed Republican accusations of an Eastern media elite.

And while he acknowledged the challenge that newspapers face in the Internet era, Milbank also encouraged students interested in writing to pursue a journalism career. As much as his Washington Sketch column has skewered politicians, he said, he is proud that it has, at times, led to positive change at institutions and in policy.

Milbank is also a political analyst on MSNBC and the author of Tears of a Clown: Glenn Beck and the Tea Bagging of America and Homo Politicus: The Strange and Scary Tribes That Run Our Government. He has been a staff writer at the Washington Post since 2000.