Green’s Dictionary of Slang

1. lowlife, criminal, frequented by unpleasant characters, thuggish.

1873		Falkirk Herald25 Dec. 6/5The hoodlum rough of San Francisco [...] jumps square and plump on your face, smashes in your nose, kicks your teeth down your throat: .
1876		Dutch Flat Forum 17 Aug. 4/3: Should farmers discard their Chinese helpers and give boys a chance, the hoodlum element would soon cease troubling municipal authorities [DA].
1886		Lantern (N.O.) 22 Sept. 2: [He] can cut a hoodlumistic figure in the public street and escape punishment for his act.
1898		Dly Gaz. for Middlesborough 23 Mar. 2/7: Skagway is now occupied by a etachment of united States troops and the reign of the ‘hoodlum’ element is at an end.
1941		V. Davis Phenomena in Crime 137: A [...] gang of burglars [...] of the hoodlum class.
1957		Kerouac On The Road (1972) 124: Ritzy’s bar is the hoodlum bar of the streets around Times Square.
1961		Kerouac letter 9 May in Charters II (1999) 289: The book was branded as being a kind of Marlon Brando Anarchy ‘Wild Ones’ hoodlum blackjacket thing.
1971		J. Mandelkau Buttons 16: Law enforcement will not tolerate their hoodlum activities.
1997		L. Pettiway Workin’ It 102: In the projects you meet all types of people, conservative, hoodlum.

2. in fig. use, working badly, acting up.

1979

‘Iceberg Slim’ Airtight Willie and Me 42: I had a helluva time willing my hoodlum organ limp again.