A formal "Drama Club" at Conroe High School was first mentioned in The Bluebell (the CHS yearbook, later renamed The Flare) in the mid-1920's. For the most part, any productions entailed a "senior play" or a "junior play." In 1922, The Conroe School presented a revue called Something Old, Something New. David Crockett High School was built in the late 1920's and was located in the building of the current Travis Intermediate School. The 1939 Flare has a photo of a play called Here Comes Charlie.

1940's:

The 1946 Flare has photos from a production called The Groom Said No!  A "speech and debate" sponsor is not listed in that yearbook, but at that time, most plays were directed by speech, debate, or English teachers. Theatre had not yet become a standard curriculum offering and it was generally extra-curricular. The 1949 Flare has  photos from three one-act plays...Mushrooms Coming Up, One Wintry Night, and Tragic Tragedy. The director is listed as Mrs. Roy Keyes.

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1950's:

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Although the most exciting CHS entertainment news of the 1950's was Elvis performing (and getting injured) on the football field in 1955,  there was a thriving drama program at the school. Under the direction of Lloyd Bond, the school produced the recent (at the time) Broadway hit, Arsenic and Old Lace in 1953. 

1960's:

The 1960's were a time of great change in the United States and Conroe was no exception. In 1963, a brand new high school opened (the current building) and the students of Booker T. Washington HS merged with CHS in 1968. Washington then became Washington Junior High. Jimmy Dorrell was listed as the sponsor in 1960, and he would appear in yearbooks in the 70's as a sponsor as well. During most of the 60's, Lucky Watkins headed the Drama program and they produced plays such as Amahl and the Night Visitors, Look Homeward, Angel and Bus Stop.

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1970's:

The dramatic changes continued into the 70's. Lake Conroe was flooded in 1973 as Conroe's population was booming. In 1976, the southern portion of the attendance zone split from CHS and began attending the new McCullough High School in The Woodlands, which was now a second high schoool for Conroe ISD. At CHS, Becky Bell (who would teach and direct until 1985) and John Harrington were sponsors of the Drama program in 1970. That year, they produced A Company of Wayward Saints for the U.I.L One-Act Play contest. Along with Becky Bell and John Harrington, other sponsors during the 70's included Jimmy Dorrell, Ivy Lipscomb, Jean Roberts, Carole Putman, and Sharon Walker. Other productions included Blithe Spirit and Death Takes a Holiday.

1980's & 1990's:

Becky Bell continued to teach and direct at CHS until the mid-80's. In the fall of 1985, Peter Dias joined the faculty of Conroe High and began a prolific and successful 14-year stint as the Director of the Theatre program. Under his direction, CHS advanced to District OAP many times as well as advancing to the Area Contest in 1991 and 1995. In the 80's and 90's, other sponsors/directors included Carole Putman, Dan Perdue and Jack McEwen.

2000's:

Dave Feranchak joined the faculty in the fall of 2000, and Becca Babbitt arrived in 2002. They remain at CHS today, teaching and directing theatre. (Click the "About CHS Theatre" menu above for more information on the current directors.) When Choir was relocated to a new room in 2002, the "theatre area" grew. The old Choir room was renovated and became CHS's second performance space, The Black Box Theatre. The Black Box productions became an integral part of the students' training at CHS. In 2009, the CHS Auditorium underwent its first major renovation since it was built in the early 60's. New lighting and sound equipment were installed, as well as motorized electric battens, a new stage floor, and new auditorium seating. The 2000's have been a very successful time for CHS Theatre. U.I.L. OAP awards have included Best Actress (for The Glass Menagerie-2001, The Importance of Being Earnest-2004, and The Lion in Winter-2013), Best Crew (for Ring Round the Moon-2007), Advancing to District (The Importance of Being Earnest-2004, Medea-2011, The Lion in Winter-2013). In 2014, CHS Theatre advnaced further than ever in the school's history, advancing to Region and winning Alternate to State with The Servant of Two Master. Other teachers who have assisted in directing U.I.L. OAP's since 2000 include Mary Mathis-Sadler, Bonnie Harwood, and Amanda Carlton (nee Broomas). In 2009, Conroe HS Theatre was selected to perform at The American High School Theatre Festival as part of The Fringe Festival in Edinburgh, Scotland. CHS Theatre students created an orginal, devised piece, Native American Tales, to perform in Scotland.

Since 2000, many musicals have been presented in conjunction with other CHS Fine Arts programs with rich histories of their own: Choir, Dance, Band & Orchestra. Music Directors have included Mary Mathis-Sadler, Jeffrey Delman, Paula Kile, Clay West, and Celeste Matthews. Choreographers: Bonnie Harwood, Fayla Chambers Curry, Amanda Bond, and Katie Ogorchock. Band/Orchestra: Bobby Heathcock, Dawn Martinez, Joseph Delosreyes, and Frank Chambers. In 2011, the musical Once Upon a Mattress earned a Tommy Tune Award nomination for Best Orchestra, and junior Cheyenne James received a Best Lead Actress nomination.

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In 2022, Sydney Boyenga and Amanda Gutierrez joined the CHS Theatre Department as brand  new Directors.

The department has also taken many educational theatre trips to New York, London, Paris, Rome,  and Florence as well as The Stratford Shakespeare Festival in Stratford, Ontario, Canada and The Oregon Shakespeare Festival in Ashland, Oregon.