Green’s Dictionary of Slang

1. (also tooth picker) a heavy club, a shillelagh, a watchman’s stick.

1811		Lex. Balatronicum n.p.: Tooth-Pick. A large stick. An ironical expression.
1821		W.T. Moncrieff Tom and Jerry II ii: Then catch – here’s the gentleman’s tooth picker, and here’s his glim.
1827		Pierce Egan’s Life in London 22 Apr. 933/1: [T]he O’Callaghans with tooth-picks in their mauleys like the branches of Old Irish Oak Trees; the O’Shaughnessy’s likewise with dusters of China in their bunches of Fives as, big as door posts; and the O'Grady's also with bits of Shilalees! [...] in their fists thick enough to floor a Mad Bull.
1834		‘Jack Downing’ Andrew Jackson 189: The gougers, and rip-roarious; the screamers who love tu rub one another down with their tooth-picks.
1835		G. Kent Modern Flash Dict. 34: Tooth pickers – Irish watchmen’s shillalies.
1843		T. Haliburton Sam Slick in England II 259: She stoops down, and catches up his staff, and says she, ‘I have as great a mind to give you a job with this here toothpick, where your mother used to spank you.’.
1848		Flash Dict. in Sinks of London Laid Open [as cit. 1835].

2. (US) a bayonet.

1848		J.F. Cooper Oak-openings (1854) II 43: The English used to boast that the Americans wouldn't ‘stand up to the rack,’ if the baggonet was set to work; but this was before we got our own tooth-picks.
1916		Yorks Eve. Post 16 Oct. 5/4: Most soldiers speak of their rifle, bayonet and cartridges as [...] ‘bond-hook’, ‘tooth pick’ and ‘Beecham’s pills’.

3. (orig. US) a pocketknife.

1845		‘Fight with Snapping Turtle’ in Martin & Aytoun Bon Gaultier Ballads 63: The noble Slingsby straightway / Drew the tooth-pick from his side.
1848		J.F. Cooper Oak Openings 271: This was before we got our own tooth-picks [...] they gave us baggonets too.
1865		H.L. Williams Joaquin 47: The habit [...] of never going even to see your next door neighbor without a ‘toothpick’ or a (lead) peablower.
1879		Longford Jrnl 18 Jan. 3/1: Buckskin Joe drawed his eleven inch toothpick, and the barkeeper subsequently swept up two fingers.
1888		H.H. Bancroft Calif. Inter Pocula 705: The typical gambler [...] is as ready with his pistol as with his toothpick.
1909		J. Ware Passing Eng. of the Victorian Era 248/2: Toothpick (American-Eng.). Clasp knife-or bowie knife. Satirical description of its formidable appearance.
1910		J. Hart Vigilante Girl 135: He loaned him his toothpick [DA].
1920		‘Sapper’ Bulldog Drummond 105: If I was you I’d put the tooth-pick away . . . You might hurt yourself.
c.1943		‘Bill O. Lading’ You Chirped a Chinful!! n.p.: Bayonet [...] Toothpick.
1948		J. Evans Halo For Satan (1949) 163: Both men died with a toothpick through the heart.
1968		(con. mid-late 19C) S. Longstreet Wilder Shore 35: He is as ready with his pistol as with his toothpick.
1980		E. Folb Runnin’ Down Some Lines 106: A knife (blade, toothpick, flick, nigger flicker, shank slicer).

4. a narrow, pointed boat.

1897

Kipling Captains Courageous 135: ‘You should see one o’ them toothpicks histin’ up her anchor on her spike outer fifteen-fathom water.’ ‘What’s a toothpick, Dan?’ ‘Them new haddockers an’ herrin’ boats.’.

5. (US) a longshoreman’s hook.

1904

C. Connors Bowery Life [ebook] He bangs his toot’pick on de bar. Toot’pick? Why, dat’s de iron hook dey use to handle freight and cases.

6. (US) a long, narrow shoe.

1906		‘This Mornin; this Evenin’ in J.F. Dobie Rainbow in Morning (1965) 176: What kin’ o’ shoes does a gambler wear? / Yaller toothpicks, cost ’leven a pair.
1911		G. Bronson-Howard Enemy to Society 20: [Wearing] long narrow, patent-leather shoes that street gamins called ‘toothpicks.’.

7. (US) a native of Arkansas [generic use of Arkansas toothpick under Arkansas adj.].

1865		in B.L. Ridley Battles and Sketches of the Army of Tennessee (1906) 460: The North Carolinians are called ‘Tar Heels’ [...] Arkansans, ‘Tooth-picks.’.
1886		Chicago Weekly News 29 Apr. 4/3: Arkansas is the Bear state and its people Toothpicks from their structure [DA].
1909		J. Ware Passing Eng. of the Victorian Era.
1946		Carey McWilliams Southern Calif. Country 172: People from Arkansas are ‘toothpicks’ [DA].

8. (UK Und.) a house-breaker’s short crowbar.

1905

in Hackney Gazette 27 Feb. 4: A thief referring to his jemmy as his ‘toothpick.’.

9. (US) a notably thin individual.

1915

Day Book (Chicago) 17 June 13/1: Blushing maidens anxious to discard the pet name of ‘toothpick’ by acquiring a few athletic curves.

10. (US black) a thin leg.

1971

(con. 1930s–50s) D. Wells Night People 118: Toothpicks. Thin legs.

11. a derog. term for something small and insignificant.

1959

E. De Roo Go, Man, Go! 117: When that truck hits any one of these toothpicks, it’s good-by daredevil.

12. (US) the penis, often but not always small; thus Irish toothpick under Irish adj.

1965

(con. 1930s) R. Wright Lawd Today 154: No toothpick guy could keep that baby satisfied.

13. (US black) a thin marijuana cigarette.

1962		P. Crump Burn, Killer, Burn! 297: All we need now is [...] a hot babe, soft music and a toothpick to be really into something.
1980		E. Folb Runnin’ Down Some Lines 171: Now you got your toothpick. Dat be a real skinny joint.
1985		‘Jennifer Blowdryer’ Modern English 79: skinny joints (n): New York PInner [...] Toothpick.
2001		D. Looser Boobslang [U. Canterbury D.Phil. thesis] 191/2: toothpick n. a thin-rolled marijuana joint.