Green’s Dictionary of Slang

1. a passenger who rides on top of a coach.

1800		Sporting Mag. June XVI 116/2: One of the outside passengers had placed himself upon the top of the coach.
1816		W. Scott Old Mortality in Waverley II (1855) 375: A wheel-carriage [...] bearing eight insides and six outsides.

2. (US prison) the world outside prison; usu. as the outside [outside adv.].

1884		Helena Wkly Herald (MT) 24 July 7/2: It was worse than boy’s play for the Sheriff to attempt to keep such a villain as Con Murphy [...] with known sympathizers on the outside, in such a play-house as the city jail.
1900		Flynt & Walton Powers That Prey 130: Wondering all the while how things were going ‘on the outside’.
1906		Sun. Times (Perth) 3 June 9/4: [from McClure’s Mag.] Did yeh tink yeh cud make yer git-away? Yer got a have a pal on th’ outside .
1914		Amer. Mag. 77 June 31–5: No one who has never lost the freedom of the ‘outside’ — that perpetual elusive dream of every convict – can realize what ‘doing time’ means.
1929		E. Booth Stealing Through Life 256: Some had shoes from ‘outside,’ polished and rubber-heeled.
1934		L. Berg Prison Nurse (1964) 96: Instead of paying off right after – like they used to – all I been getting is a beef that no sugar came in from the outside.
1943		J. Phelan Letters from the Big House 96: No workman, trusted or otherwise, was allowed to pack any case or parcel for ‘outside’ except under direct supervision.
1949		A. Hynd We Are the Public Enemies 50: Filling in his time on the outside with gas station heists.
1952		(con. 1948) G. Mandel Flee the Angry Strangers 15: I’m out, Cart, I’m calling from outside.
1958		W. Motley Let No Man Write My Epitaph (1960) 133: One of them guards [...] was a tier-to-tier pedlar. Sure ’nough. That were when I hooked up with him. I’m the contact man on the outside now.
1961		T.I. Rubin In the Life 41: Give my regards to outside.
1968		J. Alard He who Shoots Last 124: Tell me, Ragged, wot’s it like on d’outside? I can’t remember too well.
1973		T. Lewis Billy Rags [ebook] I’d got his form from a mate of mine while I’d been outside.
1977		P. Hamill Flesh and Blood (1978) 46: A narrow-shouldered Puerto Rican who was a knife artist on the outside.
1982		G. Newbold Big Huey 76: Whippy was doing the lot because he had trouble adjusting to life and situations on the outside.
1985		N. Pileggi Wiseguy (2001) 146: I had to get Paulie to talk to his son on the outside before we could convince him not to have me killed.
1992		Bentley & Corbett Prison Sl. 13: Property Anything sent to an inmate from the ‘outside,’ such as a stereo or TV.
1993		G. Disher Deathdeal [ebook] ‘You’d manage on the outside. We couldn’t’.
1995		I. Rankin Let It Bleed 86: The governor dismissed this with a wave of his hand. ‘It’s not often a suicide on the outside brings me into the equation.’.
2002		S. Maloney Something Fishy (2006) 46: Back on the outside, Syce fluctuated between low-wage jobs and petty crime.
2008		G. Pelecanos Way Home (2009) 256: Seemed to me that they’ve been in the system a long time. No one who’s lived on the outside looks like that.
2010		W. Ings ‘Trolling the Beat to Working the Soob’ in Int’l Jrnl Lexicog. 23:1 59: Although [boobslang] is specific to prisons some of its terms also form part of criminal slang on the outside.
2017		G. Gilmore Headland [ebook]He’d forgotten how efficient prison violence was. [...] Aggro on the outside was different: badly planned – if planned at all– messy and difficult to hide.

3. (US milit.) the civilian world; also as adj.

1898		H.H. Lewis Gunner Aboard the ‘Yankee’ 266: The disgruntled members of the ‘Yankee’s’ crew were composed mainly of the ‘outside’ men—men not of the Naval Reserves.
1918		D.G. Rowse Doughboy Dope 17: The boys don’t mind him, and he figures that folks on the outside are not on.
1952		J. Jones From Here to Eternity (1998) 21: He planned to come out of the Army and go right into the upper bracket. A lot of people on the Outside had their eye on him.
1967		(con. 1940s) M. Dibner Admiral (1968) 29: Navy surgeons are a pack of butchers who couldn’t make it on the outside.
2021		P. Papathanasiou Stoning 242: [of an ex-soldier] Onions had [...] been unable to handle life ‘“on the outside’.

4. (US) the world beyond one’s home and domestic life; also as adj.

1936		I.L. Idriess Cattle King 78: ‘Any ‘outside’ news?’ [...] ‘I don’t take much notice of mulga wires.’.
1939		Goodman & Kolodin Kingdom of Swing 32: There was also a regular school orchestra, but I never played in it, since I was too busy doing things on the outside.
1940		S.J. Simonsen Among the Sourdoughs 13: The Sourdoughs referred to the States as the outside.
1965		C. Brown Manchild in the Promised Land (1969) 334: I had never seen it as being possible for him to pull a chick on the outside.