this is SUCH A STRESSFUL QUESTION… i'm sorry i've let it sit for so long, but i've been thinking about it and i don't know if i have one that stands out over any of the others!! "into the woods" was my introduction to sondheim as a wee baby, so i have a LOT of affection for it, but "sweeney todd" and its obsession with death and the Dies Ire is incredible, "assassins" is entertaining and reflective, "company" makes me ACHE, "sunday in the park with george" is a beautiful character study, "follies" is a rarity in having beautiful songs for older performers, "a little night music" is a tender comedy of errors, "anyone can whistle" is a very funny tearing down of capitalistic bullshit, "a funny thing happened on the way to the forum" is shakespearian levels of comedy and dirty jokes and levity… i really, honestly couldn't choose just one. his body of work is so impressive and picking only one to shine above the others feels very wrong