Bree Olson Best Secretary Ever

Bree Olson plays a new secretary who has reportedly been involved with several other men in the office.

Is Bree Olson the best secretary ever?

Bree arrived with little fanfare. She carried a single messenger bag and wore practical shoes. Unlike her predecessors, she did not ask for a lengthy tutorial on the phone system. She simply asked for the handbook and a list of the partners' "Rules of Engagement." bree olson best secretary ever

April 14, 2026 Category: Pop Culture Retrospective / Industry Icons Bree Olson plays a new secretary who has

Here is the secret sauce: Bree Olson could act. She carried a single messenger bag and wore practical shoes

Mr. Sterling closed the file. He looked out at the bullpen where Evelyn was currently answering a call with her characteristic professional crispness. Evelyn was excellent—reliable, steadfast, and consistent. She was the bedrock of the firm.

In the same year "Best Secretary Ever" was released, Olson won several major industry accolades, including the AVN Award for Best New Starlet (2008) and the XBIZ Award for New Starlet of the Year.