* BreakawayPopHit: "Send in the Clowns" was Sondheim's first and only song to become a pop hit.
* CrowningMomentOfAwesome: As noted below, Sondheim was (and is) often considered too complex/"unhummable" to make it as a Broadway composer and lyricist. This topic is addressed in his ''Theatre/MerrilyWeRollAlong'', which [[WordOfGod Sondheim has admitted]] is somewhat autobiographical; to that end, a producer character has a solo in "Opening Doors," telling the main characters, who are auditioning their work, that their work is too inaccessible: "There's not a tune you can hum...I'll let you know when Stravinsky has a hit." Fast forward to 2013. Sondheim is now one of the most respected and admired composers/lyricists in history, with multiple Tonys, a Pulitzer Prize, and even an Oscar to his credit. HBO celebrated by putting out ''Six by Sondheim'', a documentary about his life as told through six of his songs; the songs themselves are performed in music videos. Darren Criss, Jeremy Jordan, and America Ferrera play the leads in ''Merrily'', singing "Opening Doors." And who appears as the producer in the audition portion? ''Sondheim himself.'' Think about that--he became so famous that he was able to play the very producer who once told him he'd never make it. If ''that'' isn't awesome, what is?
* CrowningMusicOfAwesome: He is, after all, ''Stephen frickin' Sondheim''.
* TrueArtIsAngsty:
** The main [[Theatre/WestSideStory competitor]] for "most famous" is a retelling of ''Romeo and Juliet''. You know, teenaged star-crossed lovers, fatal miscommunication, gang violence... what's not to love?
** We did mention that his most famous show is about a [[Theatre/SweeneyToddTheDemonBarberOfFleetStreet serial killer]], right?
** ''Bounce'' was initially a buddy comedy. It wasn't received all that well. Then it was re-tooled as ''Road Show,'' and was much darker, and received a better reception.
** ''Evening Primrose'' doesn't sound like it would be, but after watching it, you will feel uncomfortable. Because it turns out, [[spoiler: the mannequins in department stores are murdered and well-preserved people...]] And while it is one of his lesser known works, it is now considered a particular gem in his career.
* TrueArtIsIncomprehensible: ''Anyone Can Whistle'' and ''Theatre/{{Sunday in the Park with George}}'' are total [[MindScrew Mind Screws]].
* VindicatedByHistory: Sondheim's lyrics were always well-received, but his music often received lukewarm reviews from critics who thought his songs were lacking in hummable melodies, and that his failure to produce more than one BreakawayPopHit was due to his failings as a composer. Today he's usually admired equally for his words and his music.