After multiple years of experience, often including as an assistant director and/or club officer, some students are offered the chance to student direct a production. Student direction is a longstanding tradition of the theater program, though varying in capacity.

Student direction peaked in frequency from 2017–2019, averaging four student-directed productions per year. A temporary ban on student direction occurred in 2019 after three student-directed productions overlapped, resulting in disorganization and some interclub controversy. Student direction was heavily formalized starting in 2020 with new required qualifications and experience; an official application for direction was introduced in 2022. After a two-year suspension, student direction is returning in stages; in a virtual capacity in April 2021; in one-night-only capacity in January 2022; and in full with a reduced budget in May 2022, though the latter was canceled due to a public health emergency. Sense and Sensibility (2023) was the first full student-directed production since Runaways (2019).

Out of 18 known student directors from the past decade, ten have been Shakespeare directors, six have been Drama Club presidents, and three have been both. 35% of student directors from the past decade have co-directed at least one of their productions with someone else.

Student direction opportunities are historically catered to older students. 79% of the past decade's student directed productions have been directed by seniors. The remaining 21% are all juniors who directed again in their senior year.

The current record for most productions is held by former president Stephen ZagRodny, who directed three musicals and two Coffee Nights during his two terms as President of the Drama Club. ZagRodny is closely followed by Josh Schwartz, who directed the annual Shakespeare play three years in a row (2002–2004).

Despite the rareness of student directing opportunities, 1 in 4 student directors of the past decade headed more than one production, a topic that was subject to controversy in the late 2010s. Until recently, student directors (outside of Shakespeare) were chosen from a pool of upperclassmen known as the Drama Guild. Members of Drama Club could be appointed to the Guild by the president(s) after showing multiple years of commitment to the club, a largely undemocratic process that was more often influenced by favoritism than experience. The Guild came under heavy fire in early 2019, with opposers accusing the group of bias and elitism. Newly elected club leaders Maggie Zuniga and Evan Clausen abolished the Guild in August 2019 in one of their first acts as presidents.

The most recent student director was Charley Beck, making her directorial debut with Sense and Sensibility (2023).