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Entry revised for OED Online

Jack, n.1 DRAFT REVISION July 2007 
ADDITIONS SERIES 1993

    Add:    [V.] [37.] Jack the Lad [perh. cf. the expression Jack's the Lad, found in a nautical song (see quot. c1840) and in a number of other allusions in the 19th cent.], colloq., a conspicuously self-assured, carefree, and often brash young man; a 'chancer'.

[c1840 (song-title) Jack's the lad. Ibid. (refrain) For if ever fellow took delight in swigging, gigging, kissing, drinking, fighting, Damme I'll be bold to say that Jack's the lad.]
1969 J. DASH Good Morning, Brothers! vii. 111, I think to myself, now you're going to be a real Jack-the-lad with your generosity. 1970 D. CAMMELL Performance (Brit. Film Libr. S13524) R3/7 (film script) You're Jack the Lad. I've known a few performers in my time.
1981 New Society 4 June 383/3, I was always Jack the Lad{em}the one everyone liked but nobody wanted to know. 1986 J. WAINWRIGHT Portrait in Shadows viii. 61 Find somebody..who..just might be Jack the Lad. 1991 Interview Sept. 50/1 The East End urchin Tony, later a Jack-the-lad and Jack-of-all-trades.