Andy Richter Controls the Universe - Season 1 (2002)

Andy is upset at having to share his office with new employee Byron. He also doesn't like the fact that Keith has slept with the Wendy, the new secretary, on whom Andy has a huge crush.

When co-worker Charlie Rhymer dies of a heart attack, Byron blames himself (and to a lesser extend, so does Jessica). Faced with doing actual work for a change, Keith asks Andy to take Wendy to a Sound of Music This leads Andy's feelings for Wendy to awaken once more.

Andy gets reacquainted with a hot woman he had a crush on in high school, only to find out she's a bigot. Wendy takes Jessica out for a night on the town on the eve before an important meeting and Jessica subsequently turns into a party animal.