West Side Story, Leonard Bernstein's 1957 Broadway hit, features songs that generally fall into two categories -- those dealing with romance ("Maria," "Tonight," "Somewhere," etc.) and those of a humorous or sassy character ("Jet Song," "America," "Cool," "Gee Officer Krupke," etc.). But "I Feel Pretty" is the one song whose Richard Rodgers-like gaiety and elegance place it in a different category, making it seem almost out of place in this ultimately tragic musical, an updated take on Romeo and Juliet. In the story Maria, swept away in her love for Tony but unaware he has just killed her brother, sings it in the bridal shop where she works.
"I Feel Pretty" features one of Bernstein's more memorable melodies: its first four notes, deliciously rhythmic in their rising contour, repeat, then are reduced to three, then to two. This forms the core of the theme and the rest is brilliantly imagined as well. Bernstein's instrumentation colors the music with a Latin character (note the recurring rhythmic motif for brass) and so does the girls' chorus that enters midway through. Stephen Sondheim's lyrics deftly capture Maria's bliss and newfound sense of confidence, while expressing the sass and sarcasm of her coworkers ("Have you met my good friend Maria, the craziest girl on the block?"). All in all, this song must be counted among the plentiful gems from West Side Story.