40. Grabowski A hard-working, blue-collar, lunch-bucket type. Invented by Mike Ditka to describe the 1985 Bears.

39. freak Specifically, in the sense of a person who is con­temptible because of unusual behavior or appearance. First used in print by the Chicago newspaperman Finley Peter Dunne in his column “Mr. Dooley’s Chicago” in 1895. (Other uses of “freak” are centuries older.)

38. yuck it up First print appearance in Saul Bellow’s Herzog (1964).

37. dagnabbit “Darn it!” First print usage in the Tribune on August 21, 1933.
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36. mudpack A beauty treatment involving the application of mud to the face. It first appeared in print as “mud-pack” in Ben Hecht’s A Thousand and One Afternoons in Chicago.

35. pipe dream An apparent reference to the visions of opium smokers, “pipe dream” first appeared in print—with a hyphen—in the Tribune in 1890, describing the impossibility of aerial navigation.

34. Dopp kit A shaving kit. Still patented, the term is shortened from Charles Doppelt & Co., a leather-goods manufacturer formerly based at Cermak Road and Wabash Avenue.

33. home in on To move toward a goal. First printed citation in the Tribune on December 7, 1944.

32. simonize To polish, especially with wax. From the brand name Simoniz, a car polish developed by George Simon in 1910 for Simons Manufacturing Company, which was located at 2121 South Michigan Avenue.

31. puh-leeze Extension of “please” to indicate pleading or sarcasm. First print appearance in the Tribune in 1927, spelled “puhlease,” in the column “A Line o’ Type or Two,” from a reader named Kathleen begging to have her letter printed: “Puhlease, R. H. L., R. H. L., phrint me contrib, jist wance.”

30. bum rap In its original sense of a false criminal charge, the term “bum rap” first appeared in print on June 5, 1913, in the Tribune. In its extended sense of undeserved criticism or blame, it first appeared in print on September 30, 1921, also in the Tribune.

29. asswipe First print appearance in Saul Bellow’s The Adventures of Augie March (1953).

28. jinx Originally referring to curses in baseball, “jinx” first appeared in print in the Chicago Daily News in 1911. The word probably comes from either iynx, the Latin name for the wryneck bird, which was considered magical, or the title character of the 19th-century American popular song “Captain Jinks of the Horse Marines” (a connection made by the word researcher Barry Popik).

27. gank To steal or to rob. Originally an underworld term, “gank” went mainstream in the late 1990s. The first printed reference appeared in the Tribune in 1989.

26. Pullman A train’s sleeping car. Named after the Chicago railroad baron George Pullman.

25. hootchy-kootchy A seductive dance. Although it’s associated with the dancer Little Egypt at the World’s Columbian Exposition of 1893, the first appearance of the term in print is from an 1898 column by Finley Peter Dunne.

24. razzmatazz The Chicago writer George Ade first used this word in 1899, in an un-doubled-z version, as a personification of the flu: “Mr. Grip Razmataz.” The next year, he used it again in what is probably the first instance of its current meaning: showy, stylish, or dazzling.

23. pooch Although the origin of “pooch” is uncertain (it may be related to the German term of endearment Putzi), it first appeared in the Tribune in 1906 as Pooch, the name of the missing dog belonging to the White Sox first baseman Jiggs Donohue.

22. cloud nine A state of bliss. Aside from the name of a boat, the first known print citation referred to a radio show called Cloud Nine, produced in 1950 by WBBM and sponsored by Wrig­ley. The variants “cloud seven” and “cloud eight” coexisted in the early days of the phrase, “eight” being the first record­ed usage, in 1935.

21. jungle gym Originally a Chicago-based company and its brand name, spelled Junglegym. The Jungle­gym’s patent application was filed in 1921, and printed references to two-word, lowercase “jungle gym” had already appeared by 1929.

20. flea-flicker A play in football in which the ball changes hands before a forward pass. The New York Times “On Language” columnist Ben Zimmer located Tribune citations dating back to 1911 that credit the play’s invention to Bob Zuppke, then the football coach at Oak Park High School (and later at the University of Illinois).

19. Ferris wheel Named for George W. G. Ferris, who created the first example for the Columbian Exposition.

18. cafeteria When John Kruger opened a self-service restaurant at the Columbian Exposition, he named it after the Spanish word for a coffee shop.

17. props Due respect. A product of rap music, “props” first appeared in a quotation from the 19-year-old rapper Roxane Shante in the July 29, 1990, edition of the Tribune.

16. kielbasa A direct borrowing from the Polish word for any kind of sausage, “kielbasa” as referring specifically to the garlicky, peppery Polish sausage of Maxwell Street fame was first used in an English context by Saul Bellow in The Adventures of Augie March (1953).
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15. smoke-filled room The place where a decision is made in secret, perhaps corruptly. At the Republican presidential nominating convention in 1920, party leaders chose Warren G. Harding as their candidate in a room at the Blackstone Hotel that the Associated Press described with the now-famous phrase.

14. southpaw A left-handed person, especially a pitcher in baseball. Popularized by Finley Peter Dunne. Chicago sportswriters at the turn of the 20th century also provided the first recorded uses of “hit-and-run,” “pinch-hitting,” “home plate,” and “slugger.”

13. doo-wop Although the definitive first usage of “doo-wop” as a musical genre isn’t yet settled, the contenders all come from the pages of the Chicago Defender in the 1960s. (The term then was used retroactively to describe music from the 1950s as well.)

12. tho “Though,” as it was spelled at the Tribune between 1934 and 1975. Colonel Robert McCormick, the publisher of the paper, instituted spelling reforms in fits and starts, with varying degrees of success. Almost everyone today accepts “catalog” and “tranquility,” but “frate” and “iland,” not so much.

11. Mickey Finn A drink with a sedative (or, rarely, a purgative) secretly mixed in. The term comes from the name of the owner of a Chicago bar on State Street near 11th called the Lone Star Saloon. In 1903, Finn was accused of using drugged drinks to rob his customers.

10. house In reference to the style of music in which DJs mix together musical fragments on turntables. The term arose circa 1985 as a shortening of The Warehouse, a club at 206 South Jefferson Street where the form was born.

9. egghead A derogatory term for an intellectual. A 1918 letter from Carl Sandburg indicates that Chicago newspapermen used “egghead” to refer to highbrow editorial writers out of touch with the common man. In the 1950s, the word surged in popularity when the Chicagoan Adlai Stevenson was branded with the term in his unsuccessful presidential campaigns.

8. midway The section of a fair that houses the side­shows or amusements. The word was generalized from the Midway Plaisance at the south edge of Hyde Park, which served as the (small-m) midway for the Co­lumbian Exposition.

7. yuppie A somewhat derogatory term formed from the initial letters in “young urban professional.” First print usage was in the pages of this magazine, in Dan Rottenberg’s May 1980 feature on changing urban demographics.

6. two thumbs up The Chicago film reviewers Gene Siskel and Roger Ebert trademarked this phrase for movie criticism. Oppositely, in gladiatorial arenas, spectators gave a thumbs-up to indicate the combatant should be killed.

5. American dream First print reference (in its usual sense) from the Tribune, February 7, 1916: “If the American idea, the American hope, the American dream, and the structures which Americans have erected are not worth fighting for to maintain and protect, they were not worth fighting for to establish.”

4. racketeer A participant in an illegal business, i.e., a racket. Only a decade after its first print usage in the Tribune in 1924, “racketeer” was mainstream enough to appear in the name of the Anti-Racketeering Act of 1934.

3. clout Political influence, in an extension of its earlier sense of a heavy blow. The Sun-Times columnist Irv Kupcinet first used the term in print in 1958, although a 1937 citation from a book called Machine Politics referred to needing “clout from behind” in Chicago. Here's more on this word's origins.

2. skyscraper “The ‘sky-scrapers’ of Chicago outrival anything of their kind in the world,” said the Chicago Inter-Ocean newspaper in 1888—the first print usage of “skyscraper” to refer to buildings at a time when tall Chicago edifices included the 130-foot Montauk.

1. jazz The American Dialect Society’s “word of the 20th century.” The first instance of “jazz” in print referring to America’s native music appeared in the Tribune on July 11, 1915. The most recent lexicographic research says “jazz” meant “energy” or “pep” before that, and it probably traveled from California minor-league baseball to a banjo player named Bert Kelly, who started up a band in 1914 in Chicago, where the word caught on.