Pierson College's first master was Alan Valentine, then in 1935 international relations scholar Arnold Wolfers took over the role,[2] one he held until 1949.

[5] In 2004, Yale completed a year long renovation of Pierson as part of a campaign to rehabilitate all twelve colleges.

Major changes included the reconfiguration of existing suites and rooms, the move of the "Dean's" office, the addition of a new residential building, Upper Court.

[6] Pierson was elected its first rector, but unable to leave his position in Killingworth, he taught courses from his parsonage in present-day Clinton.

"[8][9][10] Pierson has been traditionally renowned for its thriving social life and once had the reputation of consistently trailing other Yale residential colleges in academic rankings.

In fact, Pierson's rallying cry at one time was, "Tyng, Tang, and GPA," reflecting Pierson's reputation for winning Yale intramural sports (Tyng), an annual drinking competition among the residential colleges (Tang), and having the lowest average GPA of all the residential colleges.

It was founded over half a century ago and nurtured by a succession of Pierson Heads including John Hersey, Quincy Porter, Gaddis Smith, and Harvey Goldblatt.

For many years the Press was located in a converted squash court in Pierson Tower, designed by Charles Willard Moore of the Yale School of Architecture.

[14] The Buttery is run by students and offers a variety of late night food options that can be ordered online.

The Fellows meet twice monthly during the academic year, generously support undergraduate activities in the college, including social events such as the annual Pierson Inferno at Halloween.

Throughout its history, the group has consisted of a diverse and dignified range of members, from poet Robert Frost to actor George Takei (Sulu of Star Trek fame) to G. D. Mostow the mathematician of Mostow rigidity theorem fame and Calvin Hill, NFL Rookie of the Year and multiple Pro Bowl selectee.

[18] The completion of the additional building, called "Upper Court", increased Pierson College's dorm space capacity from 264 to 310.

[18] A number of the songs from Dirty Projectors' Don Henley and Hernán Cortés infused glitch-opera, The Getty Address, were recorded in Pierson College, as Dave Longstreth was a student at Yale.