The four crossword solutions for the term 'West Side Story Song' are 'COOL', 'Maria', 'Tonight', and 'SOMEWHERE'. 'COOL' is a song from the musical West Side Story, sung by the Jets. 'Maria' is a love song sung by Tony to Maria, the female lead in the musical. 'Tonight' is a duet between Tony and Maria, expressing their love for each other. 'SOMEWHERE' is a song of hope and optimism, sung by the entire cast. Finally, 'America' is a song sung by the Puerto Rican immigrants in the musical, expressing their struggles and dreams.