Though not generally thought of in these terms, Stephen Sondheim and his collaborators have actually turned out some of the most socially conscious theatre in the last several decades. This started early on in his career, of course - West Side Story was an innovation not only in terms of theatrical conventions, but in touching on some of the darker facets of urban life. While Rodgers and Hammerstein had touched on race relations with South Pacific, the races in question were safely ensconced on the other side of the world. By bringing the racial tensions of the youth gangs in New York City to the stage, theatre took another step.
To continue the trend, Anyone Can Whistle is certainly a commentary on politics and government, as well as big business and society in general. Cora's mayoress is the epitome of the stereotypical politician - willing to fake a miracle to insure her continuing popularity - and willing to scheme with the best of them to keep it going.
Pacific Overatures is overtly political, of course, dealing, as it does, with the Westernization of Japan. Hal Prince had a lot to say about the political nature of the show, and in fact, this aspect was said to be more Prince than Sondheim. But the culture clash and the juxtaposition of Western ideals onto Japanese culture is an essential element of the music, as well as the visual elements of the show.
Sweeney Todd, again with Prince, turns a gothic British legend into an industrial revolution nightmare. When Prince was asked what his onstage factory set makes, he replied "They make Sweeny Todds." The original set included a blowup of a famouse British poster illustrating class differences, which was torn down by workers as the show opened. The continuing references to the inequity of class distinctions, and the evil manipulations of the Beadle and the Judge, the show's political figures, give this piece decidedly political overtones.
Sunday In The Park With George again plays with class differences a bit, and Into The Woods has been interpreted as an allegory for everything from AIDS to Nuclear War, but aside from the mild social commentary present in any modern piece, I don't believe either show was intended to be overtly political.
That certainly couldn't be said of his next show, however, since Assassins is easily his most political show to date. By examining our American "tradition" of political assassins, he managed to craft a blistering commentary on America and the American Dream. Many of the assassins in the show make valid points, and in fact, portraying them as individuals and occassionally idealists who have been seduced by the fiction of the "Everybody's Got a Right to Be Happy" American Dream instead of as a bunch of crazed wackos ruffled a lot of feathers. By the end of the show, the "sound byte" platitudes of the Balladeer ring as hollow for the audience as they do for the assassins. Nonetheless, Sondheim and Weidman manage to portray these people as individuals without glorifying them or their actions.
In Martin Gottfried's view, the show reflects Sondheim's politicization - and he cites Sondheim's rejection of the 1992 National Medal of Arts Award from the NEA as evidence of this.(He refused it due to the ongoing efforts of the political right to only give grants and awards to works that they approved of, which, in the view of Sondheim and many others, amounted to censorship). I would agree except that I don't think Sondheim waited until 1991 to be "politicized". While I don't believe he serves any specific political agenda, I believe that he has always stuck to his own beliefs and been unafraid to make social comment with his work - in 1957 or today.