Green’s Dictionary of Slang

1. to obtain services or things without paying; thus deadheadism n.

1855		Chicago W. Times 6 Sept. 1/3: The ‘fast boys’ of Chicago prefer to be members of the police force, by virtue of which they ‘dead head’ at all the unlicensed taverns [DA].
1865		G.A. Sala My Diary in America II 267: I was [...] entitled to participate to some modified extent in the privileges of ‘dead-headism’ (i.e., the free list).
1884		McCook Wkly Tribune (NE) 10 Jan. 1/4: One of the beauties and charms of an editor’s life is his dead-heading it on all occasions.
1885		Harper’s Mag. Mar. 542/1: Mr. Jefferson was not in the habit of dead-heading at hotels [DA].
1907		C.D. Stewart Partners of Providence 263: She could ’a’ dead-headed her way into a show without half trying [DA].
1945		Chicago Daily News 31 Mar. 4/2: Did it ever enter your noggin that you must [...] stop kicking about taxes, because you cannot deadhead in a democracy? [DA].

2. to ride for free; also allow someone to ride for free (as in cit. 1860); also in fig. use.

1858		Olympia (Wash. Territory) Pioneer 27 Aug. n.p.: The conductor concluded that it was the intention of the trio to dead-head one party through [DA].
1860		E. Cowell Diary 220: This line and two others have entered into a compact not to ‘dead head’ [DA].
1871		N.-Y. Trib. 2 May n.p.: In Pittsfield, recently, he is reported to have advertised that he would furnish a free pass to glory, but very few of the unrighteous population seemed anxious to be dead-headed on this train.
1879		Nat. Police Gaz. (NY) 13 Dec. 11/1: The vagrant who has deadheaded his way across the continent becomes a new man when he has reached this paradise of tramps [i.e. San Francisco].
1910		World’s Work Dec. 13748: The two brothers ‘deadheaded’ around the state (for in those days a pass was a privilege and not a crime) [DA].
1924		G. Henderson Keys to Crookdom 402: Dead heading – riding on train without paying fare.
1949		Monteleone Criminal Sl. (rev. edn).
1980		Jean Sifton Scandalous Stewardess n.p.: I’m a stewie. But this time I’m deadheading. This is my vacation.
1992		(con. 1925) F.M. Davis Livin’ the Blues 91: Next day Hazel and I deadheaded out of Kansas City.
2013		J. Stahl Happy Mutant Baby Pills 89: He was a bus driver. Riding back after a run. Deadheading.

3. to drive a cab, aeroplane etc. without its usual load or passengers.

1929		G. Milburn in Botkin Folk-Say 111: He [a taxi driver] has to dead-head all the way back [W&F].
1946		R.L. Bellem ‘Latin Blood’ in Speed Detective Aug. 🌐 At long last I spotted one [i.e. a taxi] deadheading with the flag down.
1958		in Wentworth & Flexner DAS (1975) 142/1: ‘We should charge a dollar extra to the motel because we have to deadhead back to town.’.
1981		G.V. Higgins Rat on Fire (1982) 88: Deadheaded up there like a bat out of fuckin’ hell.
1990		S. Morgan Homeboy 318: They’d dumped the aluminium siding [...] and were deadheading down to Dixie.
1991		(con. 1920s) O.D. Brooks Legs 246: He was dead-heading it from Prince Albert where he’d made an early-morning delivery.

4. to ignore.

2001

K. Sampson Outlaws (ms.) 136: I try to deadhead his questions, but he seems to like the challenge.