Dilbert is a hand drawn comic so it will never have the media reach of TV. It also tends to focus more on the details of the bureaucratic brokenness for people to laugh rather than cry at in daily life.
The office is syndicated TV with a new episode every week. It simply has high rewatch value. The broken office bureaucracy is used as a plot device rather than the focus of the show. The show focuses on characters and how they react to work life which keeps the show more funny than sad.
I would argue that Office Space actually was more effective than both of these other two. It was a one off movie from over 20 years ago that people across age groups still regularly reference. You can only watch a movie so many times. There is not much opportunity for syndication or binge watching. After you watch it 20 times 20 years ago it kind of drops out of the yearly zeitgeist.