February 1, 1839 – A new building is erected at 74 – 78 Warren Street as the Fifth Universalist Church, designed by the father of American architecture Asher Benjamin. With room for 156 pews, the total cost of construction was $29,000. The sanctuary was contained on the second and third floors of the building, while the ground level housed two retail locations at the front and classrooms in the back for Sunday school. The congregation was led by the Reverend Otis A. Skinner.

1862 – The Universalist Society merges with another congregation and vacates the building.

1863 – In February, the Hebrew congregation Ohabei Shalom purchases the building for $15,500, becoming the first synagogue in Boston.

1868 – On April 21st, the street is renamed Warrenton Street.

1887 – The Young Women’s Christian Association purchases the building for $27,500.

1889 – The building once again changes ownership when it is purchased by a Scotch Presbyterian congregation.  

1920-1933 – With prohibition, the building is sold and takes a turn in the opposite direction. The once simple and understated sanctuary upstairs, with its tall ceilings and expansive floor space, serves as the perfect hidden spot for a night club and soon the space is transformed into a popular speakeasy named “The Lido Venice”.

1933 – Prohibition is repealed and the speakeasy goes legitimate, becoming known simply as “The Lido”.

1937 – Lou Walters gets his start at The Lido, staging a show with a female impersonator and a chorus of dancing debutantes.

1937 – The Lido Venice closes and Southland, a jazz focused nightclub, opens. It featured reviews similar to the famous Cotton Club in New York. A 14 piece orchestra led by Blanche Calloway, sister of Cab Calloway, played behind fast-stepping dance numbers.

1938 – In February a devastating overnight fire guts much of the building and closes Southland temporarily. Southland reopens 6 months later and quickly becomes one of the hottest jazz clubs in the country for big-name swing bands. Performers included Louis Armstrong, Charlie Barnet, Count Basie, Cab Calloway, Fats Waller, and Duke Ellington to name a few. The NBC Radio Network, through local affiliate WBZ, broadcasts live coast-to-coast performances weekly from Southland. Many of these live recordings are still available on compact disc.

1940 – Southland closes. 

1941 – In September the building opens under the name Rio Casino. With a picturesque backdrop of Rio de Janeiro and fake palm trees that reached up to the ceiling, the club was operated by Jimmy Welansky until he sold it shortly after being charged for manslaughter as the manager of the Cocoanut Grove on the night of its infamous fire. It was purchased by vaudevillians Jack and Ben Ford and continued to thrive in the Boston nightclub scene.

1948 – In the postwar days Boston had less of an appetite for the nightclubbing lifestyle, and by ’48 the mainstage space was only used on the weekends for dance bands. Nightly entertainment was in the lounge on the first floor.

1950 – The basement space is converted into a cabaret space is opens as a separate club called Jazz at 76.

1953 – The Fords close Rio Casino and began to use the space as a function hall. Jazz at 76 closes and the space converts to a secluded gay bar.

1955 – A brief attempt is made at reviving the upstairs nightclub under the name “The Boston Ballroom”, but it meets little success.

1957 – A group of Boston University theatre department graduates, including Olympia Dukakis, found The Actor’s Company and begin performing at in a loft at 54 Charles Street, which they call The Charles Playhouse.

1957 – The Actors Company of Boston, now under the ownership of Frank Sugrue and the artistic direction of Michael Murray, has a growing reputation for producing excellent works of contemporary theatre. With their growing audience, the company needs a new and larger home. Frank Sugrue finds that home in the abandoned nightclub at 74 – 78 Warrenton Street and purchases it from the Fords. The space is quickly transformed into a theatre and appropriately renamed The Charles Playhouse. The inaugural production is Eugene O’Neill’s The Iceman Cometh.

During its tenure as a producing repertory theatre, The Charles Playhouse quickly moves to the forefront of America's regional theater movement, premiering works by Brecht, O'Neill, Pirandello and Tennessee Williams and features performances by many stars-to-be including Al Pacino, Jill Clayburgh and Jane Alexander.  

1950’s – 1970’s – The ground level of the building, having been significantly transformed from its church days, hosts a series of small nightclubs that offer a variety of entertainments. One night club in the 1962 offers “bal musette”, offering a taste of Paris. The space is known for a long time as “Charley’s” (a suitable shortening of Charles). Meanwhile the basement has been transformed into “The Playhouse Lounge”, a restaurant advertising cocktails, dinner, dancing, and entertainment on a sizeable marquee on the front of the building above the theatre marquee.

1962 – Fascinated by the large banjo show Your Father’s Mustache at the famous Red Garter in San Francisco, Harvard Graduate (and amateur banjo player) Joel Schiavone purchases the franchise rights to club and opens the Boston Red Garter in the basement cabaret theatre. After opening on September 19, Your Father’s Mustache at the Red Garter becomes an immediate sensation in Boston, and soon leads to clubs in New York City and Cape Cod. The show plays for 10 years in the Charles Playhouse Cabaret. 

Circa 1975 – A musical revue called Slap Happy opens in the basement cabaret theatre. The Tech, MIT”s campus newspaper describes the show as “Slap Happy, a comedy group, and Art Attack, a rock band, combine their talents in a musical-comedy review now playing at the Charles Playhouse Cabaret for six weeks. The show is highlighted by illusion, juggling, satire, and Stubby Malone, the world most unusual ‘midget”.

1966-1967 -The building celebrates its 10th anniversary as The Charles Playhouse by refurbishing the interior and staging an ambitious season featuring original company members like Olympia Dukakis and Edward Zang.

Late 1970’s – The Comedy Connection opens in the street level lounge and runs with great success for many years, premiering relatively unknown comedians such as Sam Kinison, Rosanne Barr, Steven Wright, and Dennis Leary, to name just a few.

1980 – Shear Madness opens in the cabaret theatre, also known as Stage II.

1980 – The building is placed on the National Register for Historic Places in recognition of Asher Benjamin having originally designed it as a church. The Charles Playhouse, in its original form as the Universalist Church, is Benjamin’s prototype for the hundreds of churches he would build in New England across the Northeast.

1988 – The Charles Playhouse celebrated its 30th anniversary with a Gala Ball honoring Jane Alexander.

Circa 1990 – The Lounge becomes a sophisticated theatre restaurant known as Roberta’s Theatre Café, aptly named for Frank’s wife.

1995 - Frank Sugrue sells the Charles Playhouse to theatrical impresario Jon Platt, who at the time operated Broadway in Boston, the Colonial Theatre, and the Wilbur Theatre. Jon brings Blue Man Group to the Charles for a limited run. As of October 10, 2013 Blue Man Group has been running for 18 years.

February 1, 2014 – Surviving nearly two centuries of change, redevelopment, fire, disreputable owners, and the urban renewal of the 1960’s, Asher Benjamin’s beautiful Greek-revival structure celebrates 175 years, watching over Warrenton Street and the ever changing city that surrounds it. As the great Boston theatre critic Elliot Norton said in 1958, “The Charles Playhouse has the proper sinned in-atmosphere to become a great theatre”.

Under the current ownership of Key Brand Entertainment, Broadway In Boston is honored to be a part of the rich and amazing history at the Charles Playhouse and is committed to preserving her for future generations.