Originally built as the Eastwood Theater in 1929, the Barrymore was founded by Richard "Sich" Slone and Tom Peterson in 1987 in an attempt to revive Madison's declining Schenk-Atwood neighborhood.

[1] The building of a large east side theater was first announced in January 1924 after the purchase of the Gottlieb Maisch property at 2090 Atwood Avenue.

[9] The first theater in Wisconsin designed specifically for sound motion pictures, the Eastwood featured a $15,000 Western Electric Vitaphone system.

WIBA radio organist Dave Welton performed on a Kilgen theatre organ "opus 4420," size 2/8, before the program, which featured the all-talking Mack Sennett comedy Midnight Daddies.

Despite the Eastwood's initial success in the wake of the stock market crash of 1929, the theater building corporation struggled with debt after the project had gone $40,000 over budget.

In the early 1930s organ recitals were broadcast live daily over WIBA,[14] and the appearances by country music stars popularized on Chicago's WLS radio drew crowds.

[21] Gisholt Machinery workers held union votes at the theater,[22] and the Madison PTA sponsored many children's film series and cartoons.

The Hilldale was quite successful with its screenings of art house and foreign films, and the next year 20th Century sought to repeat that formula with the purchase of the Eastwood Theater in 1967, having leased it previously.

Beginning in October 1967 the interior was extensively remodeled, with the octagonal tower sealed off with a drop ceiling and the auditorium gutted of its Spanish tiled porticos.

The Cinema showed art house fare like 2001: A Space Odyssey and Midnight Cowboy while also trying to retain special features for children.

[26] The X-rated movie titles on the Cinema marquee had hindered any neighborhood redevelopment,[27] and Slone and Petersen were able to find many backers who wanted to revive the area,[28] including Trinity Lutheran Church and the CEO of Madison Kipp Corporation, Reed Coleman.

Once the theater (plus its three attached storefronts) was bought for $150,000 and renovated for $100,000 more, the Barrymore Theatre (named after the famous acting family) opened on July 10, 1987.

As a one-screen moviehouse that competed with other theaters for Madison's sophisticated film-goers, the Barrymore began losing money immediately, and soon converted to a $2 budget cinema.

In order to meet a crucial bank payment, the theater launched a successful "Give a Buck" campaign in 1990,[32] but the debt still remained.