Green’s Dictionary of Slang

1. that area of Harlem otherwise known as Coogan’s Bluff, between Amsterdam and Edgecombe Avenues, between 138th and 155th Streets. As well as the rich, many black intellectuals and artists chose to live in the area, known for its grand apartment houses, once the original white population had moved out during the 1920s; thus Sugar Hiller, a resident of this area, thus attrib [sugar n.¹ (1)]; occas. of other cities.

1929		News-Palladium (Benton Harbor, MI) 26 Oct. 11/3: Whereas Strivers Row was for years the one swankiest spot, [...] the Sugar Hill section has created a new fashionable zone.
1930		N.Y. Age 16 Aug. 6/5: ‘I am glad to see all the progress being made in Harlem [...] Sugar Hill is just too bad’.
1935		Ted Yates This Is New York 5 Apr. [synd. col.] There’s a Sugar Hill ‘hot’ spot that wants [...] a piano plunker who can ‘beat it out’.
1938		Lil Hardin Armstrong ‘Harlem on Saturday Night’ 🎵 Now, all the Sugar Hillers are a bunch of killer-dillers.
1938		D. Burley N.Y. Amsterdam News 19 Feb. 17: [S]weet young ladies on the ‘Hill’ [...] live in swank apartments.
1938		Pittsburgh Courier (PA) 26 Feb. 11/1: Who is this guy ‘Daddy Warbucks’ that’s causing all the ‘Sugar Hill’ ladies to miss meals.
1941		D. Burley N.Y. Amsterdam Star-News 21 June 13: They dig each and every human on the Hill.
1944		D. Burley Orig. Hbk of Harlem Jive 114: He would own a big house on what is known as Sugar Hill.
1953		L. Durst Jives of Dr. Hepcat (1989) 5: Jackson, you may puff on down cross states, hit the high spots from Chi to sugar hill, do a statue act on 18th and Vine or tamp the stroll on Lenox Avenue. Wherever your anchor you just ain’t nowhere until you get a house party invite.
1965		(con. 1940s) Malcolm X Autobiog. (1968) 175: The Four Horsemen that worked Sugar Hill [...] there was a tough quartet.
1967		(con. 1925–9) Ottley & Weatherby Negro in N.Y. 240: The steady increase in Harlem’s population led to an overflowing of this class into the Washington Heights section, known to negroes as ‘Sugar Hill’.
1994		Hartford Courant (CT) 21 Aug. 158/1: [TV listings] Sugar Hill Harlem drug dealer quits; Mafia wants revenge.
2002		‘Touré’ Portable Promised Land (ms.) 154: We Words (My Favorite Things) [...] Crooklyn. La-La. Illadelphia. Sugar Hill. Brick City.
2019		D. Winslow Border [ebook] They’re in one of Darnell’s cribs in Harlem. Sugar Hill.

2. the brothel and ‘red-light’ area of the black part of any southern town [sugar n.⁴ (1)].

1966		Trimble 5000 Adult Sex Words and Phrases.
1986–7		Maledicta IX 148: There are black terms sugar hill and jazz joint [...] (most now obsolescent or obsolete).