Gilbert and Sullivan followed their "dark" comedy, Ruddigore, with a work that is equally grim. Sentimental and realistic, Yeomen of the Guard has less room for Gilbert's instinctive wit and cynicism; Sullivan, however, was pleased to work on a "story of human interest" with a serious undertone, a long-time desire he would ultimately fulfill with his 1891 opera, Ivanhoe.

In 1888, Gilbert and Sullivan began their new project under the working title, "The Tower Warders." Their collaboration was not the most pleasant: Sullivan infuriated Gilbert by insisting that he re-construct the second act when portions of the work were already in rehearsal. Perhaps this strained collaboration took its toll on the end product, since it never attained great popularity; although Yeomen eventually ran for 453 performances, Sullivan wrote to Gilbert: "I must confess that the indifference of the public to The Yeomen of the Guard has disappointed me greatly."

The Yeomen of the Guard, or The Merryman and his Maid opened at the Savoy Theatre in London on October 3, 1888. Critics immediately recognized the differences between the new work and Gilbert and Sullivan's earlier, "topsy-turvy" operettas. One reviewer commented on "...the new departure they have made, exchanging the grotesque fancies and wild extravagances of the past...for an altogether soberer style of opera, approaching more closely than they have done before the old school of English opera." No doubt the sixteenth century setting prompted both this approach and people's perception of it.

Sullivan's score abounds with elements drawn from earlier music and "serious" opera. The overture to The Yeomen of the Guard is one of Sullivan's two best, the other being Iolanthe. Both of these are tightly constructed and capable of being performed apart from the rest of the score. Immediately following the overture is one of Sullivan's best descriptive pieces, Phoebe Meryll's, "When maiden loves" (often referred to as her "spinning song"). This makes The Yeomen of the Guard the only of Gilbert and Sullivan's works to begin without a chorus. Ever-popular is the duet, "I have a song to sing, Oh!" introducing us to the strolling musicians, Jack Point and Elsie Mayard. Here, in which a drone accompaniment and modal flavor evoke older music.

Gems from the Act Two include, Colonel Fairfax's "Free from his fetters grim," showcasing Gilbert's alliterative ability, and the trio, "A man who would woo a fair maid," a contrapuntal tour de force. The bittersweet finale of the second act is very effective, culminating in a reprise of "I have a song to sing!" Particularly ingenious and subtle is the accompaniment during Sergeant Meryll's "Is this Phoebe?" during which he looks for his daughter. The orchestra links the segments of the hesitant voice part by continuing the melody when the voice drops out. Throughout The Yeomen of the Guard, the instrumentation is subtle, and Sullivan calls upon the full orchestra only for the tower music.

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