Green’s Dictionary of Slang

wannabe n.

also would-be
[SE I want to be ... , orig. US black, where the term simply meant a fantasist and latterly a white person wishing to be black + from surfing jargon a learner. Popularized with the rise of the pop star Madonna (Madonna Louise Veronica Ciccone, b.1958), whose fans declared, either verbally or in the way they dressed, I wanna be like Madonna]

1. an aspirant, one who yearns to be a certain individual, usu. more talented and famous than they are; of an object, a copy, something second-best.

[Barnard Bulletin (N.Y.) 28 Apr. 1: But this fact was accounted for by the generosity of the Juniors, who invited not only active members of the teams, but Had-Beens and Want-to-Bes.].
[[US]B. Jackson Thief’s Primer 145: I know a guy who just inherited over a million dollars who would give every nickel of it just to be a character [i.e. a criminal]. He just wants to be, that’s all. That’s all he cares about].
[US]L.A. Times 5 Jan. OC9/1: As for motive, Droz thinks the trio might be categorized as ‘wannabes’ – people who always wanted to be officials.
[Aus]R.G. Barrett You Wouldn’t Be Dead for Quids (1989) 9: They wouldn’t employ a lot of cream puffs and would-be’s.
[UK]Kirk & Madsen After The Ball 144: Dolly Parton wanna-bes.
[US]C. Fleming High Concept 81: So many young, hungry actress wanna-bes about.
[UK]Guardian 8 Jan. 11: The rash of Bridget Jones wannabes had opened up an important new area of readership.
[US](con. 1990s) J. Miller One of the Guys 110: ‘So how would you distinguish between a wannabe and sombody who is real?’.
[NZ]D. Looser Boobslang [U. Canterbury D.Phil. thesis] 200/2: wannabe n. 11 a skinhead gang-member. [derogatory.] 2 a M?ori skinhead. 3 an inmate new to the wing, who attempts to look muscular and staunch by adopting a boob walk. 4 a gang prospect building up his credentials in order to become a full gang-member.
[UK]G. Malkani Londonstani (2007) 127: Tim Westwood’s a wannabe, man. I hate da way dat gora tries to talk like he’s a brother.
[Aus]B. Matthews Intractable [ebook] They were also feared by some of the wannabes and plastic gangsters.
[US]T. Robinson Hard Bounce [ebook] [T]he normal regiment of scumbags, skinheads, punks, frat boys, musicians, and wannabes.
[Ire]J.-P. Jordan Joys of War 44: All the keen-as-mustard would-bes were all hot on the heels of the directing staff.
[US]S.A. Crosby Razorblade Tears 32: ‘You didn’t get that BG tattoo by being a wannabe. That’s shot-caller ink’.

2. (US prison) a young prisoner who poses as a prison-wise veteran.

[US]Bentley & Corbett Prison Sl. 91: Many young men attempt to emulate the meaner, tougher convicts by acting tough themselves. This type of convict is called a wanna be.

In phrases

Woodstock wannabe (n.) [the Woodstock Festival of 1969 (seen as the high-watermark of hippiedom) + wannabe n.]

(US campus) one whose lifestyle and attitudes are reminiscent of the hippie adj. Sixties.

[US]Eble Sl. and Sociability 16: These slang items seem just as fresh and viable as 1992’s [...] Woodstock wannabe for ‘a person reminiscent of the 1960s.’.