Sondheim's Best Lyrics in...

From Gypsy, I'd probably have to go with You Gotta Get a Gimmick, with one of my favorites being "Dressy Tessie Tura is so much more demure-er / Than all them other ladies because"

As for West Side Story, I'd probably say A Boy Like That/I Have a Love, with this verse being particularly powerful
"I have a love, and it's all that I have.
Right or wrong, what else can I do?
I love him; I'm his,
And everything he is
I am, too.
I have a love, and it's all that I need,
Right or wrong, and he needs me, too.
I love him, we're one;
There's nothing to be done,
Not a thing I can do
But hold him, hold him forever,
Be with him now, tomorrow
And all of my life!"


I don't really know Do I Hear a Waltz? very well, so I can't say anything from that.

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WEST SIDE STORY: 'Something's Coming' or 'A Boy Like That/I Have A Love'
GYPSY: 'You Gotta Get a Gimmick" or 'If Momma was Married'

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At a talk Sondheim gave in Boston, he told the audience that he thinks the single best lyric in "WSS" is:

Maria
I just met a girl named Maria.

He said that most of the rest of the lyrics in the show were dreadful and amateur. I just found that interesting, and though you might, too. :)

Re: "Gypsy," my favorite lyrics are in "Together Wherever We Go," especially this one:

Rose: And any I. O. U., I owe, you owe?
Herbie: Who, me-oh! No, you owe.
Louise: No, we owe.
Rose, Louise & Herbie: Together!

It's not the best song of the show, but I have the most fun listening to the lyrics to that song when I revisit the show (with the exception of the "Gypsy Strip," of course).

In West Side, I would have to say that "Gee, Officer Krupke" holds his best lyrics. In Gypsy, either "Roses's Turn," or "You Gotta Get A Gimmick." And in Do I Hear A Waltz I would say "We're Gonna Be Alright." Although I don't think the original cast recording has my favorite lyrics in the song, "Sometimes she drinks in bead. Sometimes he's homosexual." The scrabble recording does though.

In Gypsy, my favorite lyric is in "All I Need Now Is the Girl":

Once my clothes were shabby
Tailors called me cabby
So I took a vow, said this bum'll be Beau Brummel

Now I'm smooth and snappy
Now my tailor's happy
I'm the cat's meow, my wardrobe is a wow
Paris silk, Harris tweed, there's only one thing I need...

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DO I HEAR A WALTZ?:
I really love Someone Woke Up and Thank You So Much.

Although the song on the airplane is great, too.

GYPSY:
I really love Together or Gimmick.

WEST SIDE:
America.

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He might have been quoted saying that as well, at another point, but during the talk I attended, he said his favorite lyric was "I just met a girl named Maria." Maybe he changed his mind?

tazber, he has said on multiple occasions that he hates the Tonight lyrics because they're not things that street kids would say. Leonard Bernstein wanted poetic lyrics, but Sondheim knew that two Manhattan teenagers with gang connections would not say that "today, the world was just an address, a place for me to live in..." or "what was just a world is a star". There is no doubt that those lyrics are beautiful, but neither of their characters would be likely to say those things. "Something's Coming" and "Gee, Officer Krupkee" are songs that are more in character.

It is not a sung lyric but the best hands down is from A Little Night Music... "To flirt with rescue when one has no intention of being saved" -- it said by Fredrick to Desiree in the middle of Send in the Clowns.

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Please Hello from Pacific Overtures. Hands down.

I think Sondheim's best lyrics in WSS are in "Gee, Officer Krupke." I also love "Something's Coming."

My favorite Sondheim lyrics of all time, not in the shows you mentioned, are in "The Miller's Son."

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West Side: "Something's Coming"
Gypsy: "Everything's Coming Up Roses"
Waltz?: "What Do We Do? We Fly!"