#13—Saturday Night Live raids the improvisational comic warehouse The Second City for its inaugural cast, and the TV show’s immediate success establishes the Old Town institution as a major comedy factory. For more photos of Chicago’s artistic breakthroughs, check out the photo gallery »

In plowing through 175 years of Chicago’s history to pick the top 40 artistic breakthroughs, we looked for seminal moments that reverberated nationally or even worldwide. But in many instances, we found a pleasing subtext: an ability to make magic with a humble budget and virtual anonymity—think Mamet when he was a Second City busboy, Muddy when he was still behind the wheel of a truck.

A few caveats: Our list is light on books and buildings—both categories have been or will be examined separately in this series. (Our Top 40 Novels list is here; look for Top 40 Buildings in our next issue.) We’ve tried to tilt toward high art, not pop culture, even when diverting to pop culture venues, such as television. And we’ve ranked the breakthroughs in importance, with the highest at number 1. But, true to the city’s tradition of creative, open debate (see number 38), feel free to stand on your soapbox and rail against our choices in the comments section below.

40. September 1950 In a Time article about the pioneering Chicago TV shows Kukla, Fran, and Ollie and Garroway at Large, the NBC station manager Jules Herbuveaux explains that “Chicago goes its own way.” The budgets and equipment may be modest, and the stories are mostly ad-libbed. But the talent is spot-on, and for a moment in the late 1940s and early 1950s, the Chicago school of television rules with its recipe of informality and invention.

39. September 2000 In his breakout graphic novel, Jimmy Corrigan: The Smartest Kid on Earth, Chris Ware marries his nostalgic, geometric drawings with a narrative style that’s marked by flawed Everymen and nonlinear storylines. A fixture in Chicago’s comics community since the 1990s, Ware introduces the art world to the graphic novella form when he exhibits in the Whitney Biennial and, later, the Museum of Contemporary Art. For Ware’s thoughts on drawing comics, watch the video below:

38. August 1916 The union organizer and frequent Bughouse Square orator Jack Jones finds a home for his epitome of bohemia, the Dil Pickle Club, in a converted garage on Pearson Street (the party later moves to Tooker Alley near Bughouse Square). The freewheeling club attracts counter-culturalists of all passions and exposes them to art, dance, hobo music, and literature. Luminaries such as Sherwood Anderson, Carl Sandburg, and Ben Hecht stop by. With a capacity of 700, a stage, and a motley crew of actors called the Dil Pickle Players, the club becomes one of the city’s most popular “little” theatres and showcases local playwrights alongside the works of Henrik Ibsen, Eugene O’Neill, and George Bernard Shaw.

37. 1947 While at Roosevelt University on the GI Bill, Joe Segal starts holding jazz concerts in empty classrooms on nights when the Chicago clubs are closed. He charges students 25 cents to see the likes of Charlie Parker, Thelonius Monk, and Miles Davis. Segal never finishes at Roosevelt, but the pugnacious promoter launches a career as one of the foremost supporters of American jazz.

36. November 1995 Ira Glass tapes a chat with his mother and a story from Wired magazine cofounder Kevin Kelly for the debut episode of his idiosyncratic radio show Your Radio Playhouse, which is later renamed This American Life. No topic—be it robots or the subprime mortgage crisis—is too silly or serious for the WBEZ-rooted show, which exposes the work of journalists, comedians, poets, and modern storytellers to some 1.7 million listeners. To hear Glass discuss storytelling, watch the video below:

35. December 1958 After traveling to 24 cities, the Ebony Fashion Fair—the largest traveling show in the history of couture—comes home to Chicago, where its creator, Eunice Johnson, introduces black consumers to world-class designers such as Dior, Chanel, Lanvin, and Oleg Cassini. The wife of John Johnson, the founder of Ebony and Jet magazines, Eunice doesn’t just borrow the clothes for her lavish shows, she buys them, and she helps boost the careers of black designers such as Patrick Kelly and Stephen Burrows.

34. September 1900 A professional roustabout named L. Frank Baum writes a tale about a tin woodsman who lives in a magical world called Oz—a fanciful place inspired by Baum’s visits to the World’s Columbian Exposition of 1893. He hands his story to a newspaper illustrator, W. W. Denslow, who produces the most lavish pictures yet created in American children’s literature. The Wonderful Wizard of Oz becomes a bestseller—and America has its first homegrown fairy tale.

33. 1967 The fiery young Englewood poet Haki Madhubuti—then called by his birth name, Don L. Lee—meets the poet Gwendolyn Brooks at a poetry workshop in Woodlawn, and a friendship blossoms. The pair proselytize the art of poetry in South Side bars, and under the banner of Third World Press, Madhubuti ultimately publishes ten collections of Brooks’s writing, including her only novel, Maud Martha. In 2006, Madhubuti becomes the first black publisher to land a book on the top spot on The New York Times bestseller list, with The Covenant with Black America, edited by Tavis Smiley. For Brooks’ poem, "We Real Cool," watch the video below:

32. June 2000 Richard Wright, a dealer of 20th-century furniture and art, hoists the gavel for his first auction, featuring designs by Alvar Aalto, George Nelson, Edward Wormley, and Charles and Ray Eames. Wright quickly builds an auction category for modern design and, not content to focus only on historically accepted work, begins to use his market prowess to nurture new contemporary designers.

31. December 1957 At the urging of his fellow folkie Bob Gibson, a 20-something musician named Frank Hamilton begins performing at the Left Bank–inspired folk club the Gate of Horn. There, Hamilton meets the singer Win Stracke and the folk enthusiast Dawn Greening and, with their support, opens the tiny Old Town School of Folk Music in a dingy bank building at 333 North Avenue. The school becomes a musical institution, inspiring generations with its group classes, jam sessions, and performances.

Photograph: (Saturday Night Live cast) © NBC/courtesy of the Everett Collection

30. Fall 1937 The filmmaker, photographer, and graphic designer László Moholy-Nagy flees Nazi Germany for Chicago and, on the recommendation of his former collaborator Walter Gropius, begins teaching Bauhaus principles in a mansion that was once owned by Marshall Field. The New Bauhaus—which is later reorganized and renamed the Institute of Design in Chicago (now part of IIT)—strongly influences the genre of abstract black-and-white photography: Notables such as Harry Callahan, Aaron Siskind, Wynn Bullock, and Frederick Sommer all pass through its doors.

29. May 1972 Chicago cashes in on its reputation as a petri dish for antimainstream art with a large-scale exhibition of three generations of Chicago imagists, starting with the postwar painter Leon Golub and moving through Karl Wirsum and Jim Nutt. The massive Museum of Contemporary Art show is timed to coincide with the publication of the Franz Schulze book Fantastic Images: Chicago Art Since 1945, which finally gives a name to the color-splashed pop-meets-surrealism movement that flourished here. Fourteen galleries host companion shows, and the citywide push renews public interest in the visually arresting genre.

28. October 1995 Plagued by financial troubles and its near dissolution after the death of its founder, Robert Joffrey, the Joffrey Ballet cuts ties with New York and comes to Chicago seeking refuge and reinvention. An active women’s board embarks on a high-profile fundraising effort. Over time, audiences grow, proving false the notion that Chicago only supports modern and contemporary dance.

27. June 1993 Curators at the 11-year-old Mexican Fine Arts Center Museum (now the National Museum of Mexican Art) assemble an exhibition of socially and politically charged works by 20 contemporary Mexican American artists—think Da Vinci’s Mona Lisa reinterpreted as the Virgen de Guadalupe (Mona Lupe, by Cesar Augusto Martinez). After Chicago, Art of the Other Mexico travels to New York, California, and three cities in Mexico, and the Pilsen museum becomes a prime example of “first voice”: an ethnic institution leading the interpretation and presentation of art from its culture.

26. September 1975 The Chicago Sun-Times film critic Roger Ebert partners with the Chicago Tribune reviewer Gene Siskel for a TV show on WTTW that will eventually be called Siskel and Ebert. The contentious pair demonstrate immediate onscreen chemistry—and influence. In their thoughtful, if adversarial, style, they popularize the erudite art of movie reviewing, champion independent films and first-time directors, and tackle issues such as film colorization, the MPAA rating system, and product placement. For some hilarious Siskel and Ebert outtakes, watch the video below:

25. January 1938 Refusing to be a “polka dot”—her term for the one or two black dancers in a majority white company—Katherine Dunham throws her artistic energy toward choreographing full-length works for African American dancers. Inspired by a trip to Haiti and the Caribbean while a student at the University of Chicago, she debuts a ballet called L’Ag’Ya at the Great Northern Theater in the Loop. The blend of Afro-Caribbean dance and theatre is a sensation—and offers audiences the first real glimpse of Dunham’s anthropological technique, which inspires more than 90 of her own dances as well as generations of dance makers. To watch Dunham dance, watch the video below:

24. April 2002 Wilco releases its masterpiece, Yankee Hotel Foxtrot, on the Nonesuch label. The album is hailed instantly as a classic—sweet vindication for the band, which only a year prior had been told by its previous record label that the music was not commercially viable. The album sells 55,000 copies in its first week and lands a coveted spot at the top of the Village Voice critics’ list for recording of the year.

23. November 1954 Known to the American public only through recordings, Maria Callas makes her United States debut at the Civic Opera House with the new Lyric Theatre of Chicago. Her chameleonic performances in three dramatically different operas—Lucia di Lammermoor, Norma, and La Traviata—cement her as a star and put the fledgling Lyric on the national map.

22. July 2004 Despite multimillion-dollar cost overruns and visual anarchy (the result of allowing large donors to drive aesthetics), the new Millennium Park introduces the masses to interactive public art and reignites the city’s design scene. Of particular note is Cloud Gate, by Anish Kapoor. Under contract to produce a work that could last for 1,000 years, Kapoor collaborates with a structural engineer on the 110-ton polished steel jellybean, which, in reflecting the city, offers observers a sweeping view of a century of architectural brilliance.

21. March 1913 For 24 days, the Art Institute of Chicago hosts 634 works from New York’s Armory Show, a presentation heavy on cubism, futurism, and French postimpressionism. The exhibition—particularly the work of the cubists—is met with vitriol and concludes with a group of art students trying to burn a figure of Matisse in effigy. Yet the event draws 188,000 visitors and introduces many prominent Chicago critics, artists, and collectors to 20th-century art.

20. February 1967 The WFMT radio host and professional conversationalist Studs Terkel goes into neighborhoods with his tape recorder and interviews 71 everyday Chicagoans—“people who make the world go around”—for Division Street: America. The book, a bestseller, helps establish oral history as a literary form. For more from Terkel, watch his interview with Charlie Rose below:

19. August 1967 Bribed by souvenirs, such as a White Sox uniform and an Indian war bonnet, and courted in repeated visits from the Chicago architect William Hartmann, the Spanish artist Pablo Picasso finally agrees to design his first large-scale civic sculpture. When the five-story steel monument is unveiled in Civic Center Plaza in August 1967, the public is perplexed—Is it a bird? A woman walking a dog?—but ultimately won over with news that the 85-year-old artist has handed back his check and donated his work to the people of Chicago.

18. January 2007 Two years after August Wilson’s death, the Goodman Theater stages Radio Golf, the coda in Wilson’s effort to dramatize the African American experience. A champion of new plays, the Goodman earns the distinction of being the first theatre in the country to produce all ten plays in Wilson’s Pittsburgh Cycle. The Kenny Leon–directed production travels largely intact to Broadway, where it garners four Tony nominations.

17. 1917 Rebelling against the American inclination for formal gardens, the Danish landscape architect Jens Jensen proposes what will be his greatest achievement: the 144-acre Columbus Park on the western edge of Chicago. With the eye of an artist, he fashions meadows and groves out of native flowers, shrubs, and trees. An early conservationist, Jensen helps shape many of Chicago’s major public places, and his efforts change the style of American landscape architecture.

16. October 1912 At 51, the Chicago poet Harriet Monroe founds the magazine Poetry to rescue what she calls the “Cinderella of the arts.” In her inaugural issue, she dubs the London-based poet Ezra Pound her first foreign correspondent. Though not rich, Monroe solicits 100 wealthy Chicagoans to each pledge $50 a year for five years, and the magazine becomes the headquarters and spiritual home of modern poetry.

15. April 1919 A decade before the works land in an American museum, the Chicago Arts Club curators Rue Carpenter and Alice Roullier mount an exhibition of French post­impressionists that includes Van Gogh, Cezanne, Matisse, Dufy, Signac, Derain, Seurat, and “Paul” Picasso, as he was named in the catalog. This is the second American showing of Seurat’s revolutionary “divisionist” work Sunday Afternoon on the Island of La Grande Jatte. (The Art Institute won’t acquire it until 1926.) The show establishes Chicago’s reputation as a supporter of provocative new art.

14. June 1974 Stuart Gordon, the founder of the Organic Theater and an early nurturer of Chicago playwrights, works with the young local actor-writer David Mamet to fashion a series of sketches into the full-length theatre piece, Sexual Perversity in Chicago. The language is foul, but Mamet demonstrates a poet’s flair for stringing together street vernacular in a rhythmic way. After he volunteers to be Organic’s playwright-in-residence and Gordon turns him down, Mamet marches his next work, American Buffalo, to the Goodman, where it becomes a hit, launching him as one of the foremost American playwrights of the 20th century.

13. 1975 Saturday Night Live raids the improvisational comic warehouse The Second City for its inaugural cast—called the Not Ready for Prime Time Players—and nets rising stars John Belushi, Dan Aykroyd, and Gilda Radner. The TV show’s immediate success establishes the Old Town institution as a major comedy factory, and Chicago-style sketch comedy reigns as a new format for TV. For more on how famous comedians got their start with Second City, watch the video below:

12. May 1885 The Chicago architect William LeBaron Jenney completes construction on the ten-story Home Insurance Building, considered by some the world’s first skyscraper, at Adams and LaSalle streets. Working with pressed brick and stone, Jenney promises a skittish public that the structure will be “strictly fireproof.” Demolished in 1931, the building is one of the earliest examples of iron-and-steel-frame technology.

11. Fall 1971 Under the direction of Sir Georg Solti, the Chicago Symphony Orchestra embarks on a six-week tour of Europe and takes the continent by storm. In Milan, Solti is warned to expect a temperamental public, but instead of boos, the audiences cry “bis,” the Italian request for an encore. The tour rallies a local funding base of donors—both individuals and corporations—and cements the orchestra’s reputation as an international force.

10. October 1933 Ernest Hemingway’s “Marlin Off the Morro: A Cuban Letter,” a spirited tale about a fish that got away, runs in the debut issue of Esquire, published and edited by two Chicagoans, David Smart and Arnold Gingrich. Thus begins a long relationship between Esquire (which remained in Chicago until 1950) and the Oak Park–born author—a relationship that helped Esquire establish itself as a premier men’s literary magazine.

9. August 1922 Lured by the promise of $52 a week, Louis Armstrong packs a suitcase and his trumpet and takes the train from New Orleans to Chicago to play with his inspiration and idol, Joe “King” Oliver, and his Creole Jazz Band. By Armstrong’s second night in town, audiences at the South Side dancehall Lincoln Gardens are demanding to hear “the youngster” play. Armstrong’s time in Chicago permeates his style: Under the tutelage of Oliver, he learns to follow the melody, and with the pianist Earl Hines, he gains the confidence to go his own direction rhythmically. Backed by Hines and the session groups the Hot Five and Seven, Armstrong records songs that showcase his furious solos, bold improvisations, and vocals—an effort that’s considered the artistic pinnacle of a virtuosic career.

8. August 1933 With the aim of developing and preserving spiritual songs, the pianist and gospel songwriter Thomas Dorsey convenes the first national assembly of gospel choirs and choruses at Pilgrim Baptist Church at 33rd Street and Indiana Avenue. The Chicago Defender calls the gala songfest “a new epoch in the musical world,” and Dorsey is credited with reviving and formalizing gospel music as an art.

7. October 1982 New York critics and audiences first learn of Steppenwolf when Sam Shepard’s hit play True West lands at the Cherry Lane Theatre. The stars, John Malkovich and Gary Sinise, become the toast of Off Broadway, and the production introduces the country to Steppenwolf’s visceral acting style.

6. July 1955 In a room off a Hyde Park bar, a cast that includes David Shepherd, Paul Sills, Roger Bowen, Elaine May, and Barbara Harris stages a satirical revue based on current events. The audience is encouraged to blurt out random character and topic suggestions, which the ensemble improvises using a quickfire method developed by Sills’s mother, the acting coach Viola Spolin. The evening inspires a theatre troupe named The Compass; after the group dies two years later, Sills, Bernie Sahlins, and the actor Howard Alk create a spinoff, The Second City, which opens its doors in 1959.

5. Fall 1930 Using techniques of northern European Renaissance painters and the stark backdrop of his native Iowa, an unknown artist named Grant Wood paints his sister and the family dentist as a weathered farmhand and his spinster daughter. When American Gothic goes up as part of an exhibition of American paintings at the Art Institute in the fall of 1930, it wins a bronze medal and a modest $300—but creates a national stir for its prim portrayal (some say satirization) of Midwestern farm life. By the time the controversy settles, the painting is on its way to becoming one of the most famous—and parodied—examples of the regionalism style.

4. 1893 At the World’s Columbian Exposition, Frank Lloyd Wright discovers Japanese art and architecture while touring a sprawling exhibition and ornamental garden designed by the imperial architect for the fair’s Empire of the Mikado. This ignites Wright’s lifelong obsession with traditional Japanese elements such as low-pitched double roofs and shakkei—using a door or window to frame a landscape outside—and two signature elements of Prairie style are born.

3. July 1909 Daniel Burnham and his assistant, Edward Bennett, publish their Plan of Chicago in a 156-page book elegantly illustrated by Jules Guerin. Commissioned by a cadre of wealthy businessmen, the plan threads together existing public land, calls for additional lakefront parks, widens boulevards, creates Michigan Avenue and Wacker Drive, and establishes suburban forest preserves. Though only partially implemented, Burnham’s vision becomes a model for metropolitan planning and gives Chicago’s citizenry back something that is rightfully theirs: public space.

2. 1938 With his beloved Bauhaus quashed, European commissions dry, and the Nazi regime entrenched in power, the German architect Ludwig Mies van der Rohe settles in Chicago to head the architecture school at the Armour Institute of Technology. He is not only charged with elevating the school’s academic stature but is asked to create an all-modern master building plan for the growing institution, which becomes the Illinois Institute of Technology in 1940. In all, he designs 20 buildings for the campus, including the monumental Crown Hall, and in doing so, ushers in a second golden age for Chicago architecture.

1. April 1948 Leonard Chess, a white Polish immigrant who owns a Bronzeville nightclub, records a few songs by Muddy Waters, a black truck driver who migrated to the South Side from Mississippi and has been sitting in on “country blues” sessions that feature the piano and acoustic guitar. Waters begs to let his electric guitar rip on two originals, “I Feel Like Going Home” and “I Can’t Be Satisfied,” and when the effort lands on Billboard’s “Most Played Jukebox Race Records” chart, Chess’s company, then called Aristocrat (later Chess Records), claims its first national hit. The partnership boosts the careers of both men and changes the direction of the music business. Waters becomes a sensation, and his success sparks the rise of the postwar electric blues. With his brother, Phil, Chess chaperones more black musicians with blistering talent (Howlin’ Wolf, Chuck Berry, Etta James) into the mainstream and injects popular music with the powerful progressions of blues and R & B. Check out Chess’s "I Can’t Be Satisfied," played by Muddy Waters, in the video below: