As requested by musical theatre aficionado @ajt. Picking just a few was hard but I think I did an admirable job. Feel free to suggest more!
  1. I Am What I Am - La Cage Aux Folles
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    A torch song that morphs into a ballad, this song from a musical way ahead of its time spawned a disco rendition and an enduring anthem for LGBT people and anyone who feels marginalized in society. Here Albin, a middle-aged French drag queen, has just learned that his adopted son does not want his fiancée's family to meet him - his gay lifestyle is an embarrassment. He draws five simple words out of his deep wound and turns them into a rallying cry.
  2. We Do Not Belong Together - Sunday in the Park with George
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    Sunday is full of tearjerkers, but this one is especially devastating. What I love about Bernadette Peters is that despite her voice's innate power and clarity, there is always something quivering and vulnerable about it that suggests that by singing, she is laying her entire soul bare for you. Here her character Dot painfully breaks up with her lover George - she has realized he will never love her like he loves his art.
  3. The I Love You Song - The 25th Annual Putnam County Spelling Bee
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    What's awesome about Spelling Bee is that the "adults playing neurotic children" concept goes from comedically jarring to heartbreakingly touching. Here, 11 year old Olive, abandoned by her mother and ignored by her father, indulges in a beautiful fantasy that draws colorful musical poignance out of the simple phrase she has never heard her parents say: "I Love You." Where composer William Finn and these actors take those three words is just unbelievable.
  4. Your Daddy's Son - Ragtime
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    The start of Audra McDonald's long and illustrious career was in Ragtime, a show that she dies halfway through and still manages to steal the entirety of. In this ditty, possibly the creepiest song ever sung to a sleeping child, her voice soars as she holds the baby she literally just attempted to bury alive in the ground. MUSICAL THEATRE! Her tenderness and despair crests over her in this song, neutralizing her innate hope. Tears. Absolute tears.
  5. Wheels of a Dream - Ragtime
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    ....but things look up for Audra (known in the show as Sarah) when Coalhouse, her lover and father of her baby, returns and they plan a life together. This number kills me because their boundless optimism for what America will bring them is so beautiful, and of course completely ill-fated. Within 15 minutes of stage time Sarah will be dead and Coalhouse's beloved Model T destroyed. Oops.
  6. Sailing - A New Brain
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    A stunning and overwhelming yet beautifully simple love song from a man to his boyfriend, who is suffering from a brain tumor. With whatever time they might have left, the character wants to make the most of it. Sung beautifully here by Norm Lewis, musical theatre demigod/former Olivia Pope love interest.
  7. Send in the Clowns - A Little Night Music
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    Easily Stephen Sondheim's most famous and tragic song (and one he allegedly wrote in about a day during an out-of-town tryout), this has been recorded by everyone from Barbra Streisand to Frank Sinatra to Catherine Zeta-Jones. In my opinion Judi Dench (yup) provides the definitive rendition. You can see her aging character Desiree's last chance at happiness slip away, and her life's disappointments become a wistful laughing matter.