Green’s Dictionary of Slang

1. (US) the buttocks, the posterior.

1931		J.T. Farrell ‘Big Jeff’ in Short Stories (1937) 52: Big Jeff [...] had to blow town or get his old tomato pumped full of bullets.
1935		(con. 1920s) J.T. Farrell Judgement Day in Studs Lonigan (1936) 702: Tell him to shake his tomato out of bed.

2. (US) a fool.

1923		H.C. Witwer Fighting Blood 273: This tomato tells me the owner didn’t know he was doin’ business with a combination of box fighters.
1938		C. Beaton Cecil Beaton’s N.Y. 25: One which citizens without as many potatoes as this guy seems to have in his pocket, would do well to avoid if she gives them the eye, or I’m a tomato.

3. (orig. US) an attractive woman.

1922		Ogden Standard Examiner 12 Apr. 6/5: There was one wally I was goofy about, but while I was necking with him, Harry caught a tomato, so he says, ‘Let’s blouse’.
1938		J. Weidman I Can Get It For You Wholesale 145: This tomato I got up here with me, she don’t like automobiles.
1946		J. Adams From Gags to Riches 239: ‘Who’s da tomata?’ ‘Darling,’ I said to Babs, ‘I’d like you to meet B.S. Pully.’.
1957		R. Prather Always Leave ’Em Dying 25: It was a woman, a doll, a sensational tomato who looked as if she’d just turned twenty-one.
1962		T.F. Jones Stairway to the Sea 55: Hamlet is big buds with this other cat, Horatio, and he’s got a tomato named Ophelia on the string.
1963		M. Spillane Return of the Hood 12: I was trying to figure her for a high class hooker or a tomato with a hot item for sale.
1970		G. Greer Female Eunuch 266: Who likes to be called dry-goods, a potato, a tomato or a rutabaga?
1992		Zora Young ‘Football Widow’ 🎵 Hand me a sexy tomato / Wanna go out, dance along by the two.
1999		Guardian Rev. 23 July 2: He runs into this tamayto [...] and she makes a pass at him.
2001		cwnews ‘Events’ in Eye on CameraWare III Apr. 🌐 I entered a couple of communities and threw back a couple of glasses of eel juice, just to get a make on the place. As I sucked back on a little hooch, I began to notice all the cute tomatoes around me.

4. (US) an attractive (effeminate) young man.

1932

‘R. Scully’ Scarlet Pansy 150: Here one heard fruit, banana, meat, fish, tomato, cream, dozens of everyday words used with double meaning.

5. (US Und.) a pimp.

1935

A.J. Pollock Und. Speaks.

6. (US Und.) a prostitute.

1939

D. Maurer ‘Prostitutes and Criminal Argots’ in Lang. Und. (1981) 117/1: bladder. An unattractive prostitute. Also [...] tomato, each expressing varying degrees of unattractiveness.

7. (US Und.) a stolen car.

1948

Mencken Amer. Lang. Supplement II 724: Bender, tomato or puppy. A stolen car.

8. (US) a woman.

1931		D. Runyon ‘Dream Street Rose’ in Runyon on Broadway (1954) 46: An old tomato by the name of Dream Street Rose comes in.
1945		Detour [film script] Give a lift to a tomato, you expect her to be nice, don’t you?
1963		in T.I. Rubin Sweet Daddy 54: She was sort of a nympho [...] A tomato that really liked to ball.
1975		L. Rosten Dear ‘Herm’ 8: I think I will be at least 100 bucks in the red if this cockamamy tomato goes on.
1989		H. Rawson Dict. of Invective (1991) 14: Women, again, often are characterized as edible objects. Cookie, cupcake, lamb chop, sugar, sweetie pie, (hot) tamale, tart, and tomato.
2001		‘Randy Everhard’ Tattoo of a Naked Lady 39: The robust tomato saw it first. ‘Oooh, looky!’ she goes.

9. (US) a fellow, a ‘guy’.

1941		D. Burley N.Y. Amsterdam Star-News 3 May 13: I lamped some real bad tomatoes.
1949		J. Archibald ‘State Penmanship’ Popular Detective Jan. 🌐 ‘Funny lookin’ tomater, ain’t he?’ Kelly played the flash on the deceased’s face.

10. (US) the vagina.

1970		J. Bouton Ball Four 232: ‘Hiya, blondie? How’s your old tomato?’.
1999		J. Stahl Perv (2001) 287: Bobby, get down here and eat my shaved tomato.
1999		R.G. Barrett Wind & Monkey (2013) [ebook] ‘[I]t turns out she’s got the giant, enormous tomato. A bit of vaginal trauma’.

11. (N.Z.) a NZ$100 bill.

2001

D. Looser Boobslang [U. Canterbury D.Phil. thesis] 190/2: tomato n. 1 a $100 note.