Chicago Mob Speakeasies

Massacres, trap doors and Chicago jazz. It’s the way Al Capone and his Chicago Outfit experienced Chicago in the 1920s. The rich, bloody mark that Chicago’s mob bosses left on the streets is still — sometimes begrudgingly — remembered by many. Recently, we took a trip to Chicago to discover where the old speakeasies used to be and where the St. Valentines Day Massacre occurred, grabbing a pizza along the way.

Room 21

Don’t be fooled by the ornate designs, this restaurant has a dirty history. At the peak of Capone’s business, this was his largest speakeasy and brewery in all of Chicago.

At first glance, Room 21 is simply an upscale American restaurant with a large bar and a wide-open patio. In one corner, however, lies one of Capone’s best-kept secrets. “There was the original foundation here,” Manager John Nowowiejski said, motioning to the corner at the end of the bar. “But when we were doing some work putting the plumbing in for the cappuccino maker, we found something. So Jerry Kleiner, the owner said ‘tear it all down’ and we found this passageway.”

The passageway, now lit with an incandescent red glow, narrowly follows the edge of the building. You can see the original brick on either side, claustrophobically coercing you up the stairs. And under the newly added stairs, the top corner of a door peeks out. Leading to the street, the door was probably one of Capone’s exits.

Another door existed at the top of the stairs. “At the end of the passageway, we found a door with the number 21 hanging on it,” Nowowiejski said. “And that’s how we got the name of the restaurant.”

“We actually don’t know much of what happened here,” Nowowiejski said, opening the door at the end of the hall. The inside has been radically changed to a room with classical artwork and a table overlooking the kitchen. “The unknown about it adds to the mystique.”

Not only did Room 21 house Capone’s largest brewery, it was one of his largest busts. Eliot Ness of the Untouchables, the Chicago police group designed to deal with the mafia, led his team into the speakeasy with a 10-ton truck and seized two hundred thousand gallons of alcohol.

Getting there: Take the red line to Cermak/Chinatown and turn left until you get to South Wabash. 2110 S. Wabash St.

Green Mill Cocktail Lounge

To see one of Al Capone’s favorite clubs, head over to the Green Mill Cocktail Lounge. His booth is the first one you see walking past the old jazz posters and decorative walls. And don’t expect a menu; everything served here comes in a glass, not on a plate.

“Al Capone was also a regular here,” owner Dave Jemilo said. “He would sit in a booth by the wall so he could see both doors. That’s what you do. There was a way people could come from behind and get him, but he had guards to check his back.”

And if Capone ever needed a quick escape route, he had his own way out. “There was a trap door for him behind the bar where he could escape if need be,” Jemilo said. “There was a series of tunnels and passageways that would lead outside. I’m the only one with the key, and I wouldn’t let you down there anyway.”

Jack “Machine Gun” McGurn, one of the men responsible for the St. Valentine’s Day Massacre, was a part owner of the club at one point. And when the headlining singer left for a rival club, McGurn took action himself.

“His favorite singer at the club was Joe E. Lewis, but Lewis was offered a better deal at Rendezvous Club,” Jemilo said. “McGurn told Lewis that he signed a deal for life at Green Mill, but Lewis quit anyways. So a week later, McGurn went to Lewis’s hotel and cut off his tongue and slit his vocal cords so he could never sing again. He almost died, but he eventually came back as a comedian and became a famous comic.”

Frank Sinatra later immortalized Joe E. Lewis in The Joker Is Wild, a movie detailing the whole fiasco.

Getting there: Located off the Lawrence stop on the Red Line in Uptown, the Green Mill Cocktail Lounge is the perfect place for a drink before or after a show at the Aragon. 4802 N. Broadway Ave.

Chicago Pizza and Oven Grinder Co.

The St. Valentine’s Day Massacre of 1929 was the turning point for the infamous Chicago Outfit. While Capone was enjoying a vacation in Florida, part of his south-side gang, two dressed up as police officers, allegedly lined up four of Bugs Moran’s north-side gang inside a garage. With Moran’s gang against the wall, Capone’s henchmen opened fire. Jack “Machine Gun” McGurn, part owner of the Green Mill Cocktail Lounge, was the purported leader of the shooting.

Across the street on the second floor of what was a boarding house, two other members of Capone’s gang kept watch. And today, on the first floor, is Chicago Pizza and Oven Grinder Co., a unique and original restaurant located in the middle of Lincoln Park.

You can still see where the massacre took place, but there is no garage left. “Mayor Daley tore down the garage and now it’s an empty lot,” Manager Cathy Gallanis said. “No plaque or anything about it. He didn’t want a reminder of what happened.”

As for the pizza here, it isn’t what you would normally expect, Gallanis said. It’s called pizza pot pie. “We take a ceramic bowl layered with our homemade dough and then add a layer of cheese. Then we ladle in our homemade sauce, with or without sausage, and throw in whole, fresh mushrooms. We put some white or wheat dough on top and cook it. Then at the table, we flip it over and that’s it.”

Recently featured on Rachael Ray, Chicago Pizza and Oven Grinder Co. will continue to serve its unusual cooking. “In a world of franchises, we try to be unique and original,” Gallanis said. “We’ve had the same menu since we opened in 1978.”

Getting there: Get off at the Armitage stop on the brown line and head east on Armitage Street then north on Clark Street to pay homage to one of the most violent events of the 1920s, and one of the most forgotten places too. 2121 N. Clark St.

Tommy Gun’s Garage

To literally relive the Prohibition era (the drinking side of it, not the dry), head south to Tommy Gun’s Garage. Owners Kris Adams and Sandy Mangen emulate the original speakeasies to a tee, not leaving out any details.

“We’re running an illegal speakeasy here,” Adams said. “There are no signs out front, and we have a doorman to check everyone who comes in. He wears gloves so he won’t leave any fingerprints and he will only let you in if you say the password.”

The servers are not just servers, but gangsters with holsters or flappers with dresses. After dinner, the entertainment begins. “The show is basically a musical comedy review, “ Adams said. “We have the sing and dance numbers in the beginning and after that we have vaudeville skits with an Abbott and Costello type act. The show has a lot of audience involvement. At one point, the cops show up and bust everybody there.”

Getting there: Get off the El at Cermak/Chinatown on the Red line and turn left. Reservations are required, so call (312) 225-0273, and don’t forget the password. 2114 S. Wabash Rd.

For its tame Midwestern reputation, Chicago has a rich and violent history riddled with secrets and hidden tunnels. Next time you go downtown, add interest to your usual destinations by making a night of a mafia hangout. Your historical knowledge will impress your friends, your date, or your parents alike — and chilling where Capone chilled? Badass.

Louie Prima..A Chicago Mob Favorite

He has crooned many a Mobster

A tireless showman and an underrated musical talent, Louis Prima swung his way to icon status thanks to an irresistible, infectious sound whose appeal translated across generations. Nominally a swing artist, Prima's distinctive sound also encompassed New Orleans-style jazz, boogie-woogie, jump blues, R&B, early rock & roll, and even the occasional Italian tarantella. Regardless of what form his music took, it swung hard and fast, with a rolling, up-tempo shuffle beat that helped some of his earlier material cross over to R&B audiences (his songs were also covered by jump blues artists from time to time). His greatest period of popularity coincided with his marriage to singer Keely Smith, whose coolly sophisticated vocals and detached stage manner made a perfect counterpoint to Prima's boisterous presence: mugging, clowning, and cavorting around the stage with the boundless enthusiasm of a hyperactive boy. Prima's band during this time was anchored by tenor saxophonist Sam Butera, whose grounding in jump blues and New Orleans R&B was a perfect match. Perhaps because Prima refused to take his music too seriously, sober-minded jazz critics often dismissed him as a mere entertainer, overlooking his very real talent as a jazzman. He was a capable, gravelly-voiced singer modeled on Louis Armstrong, boasting a surprising range, and was also a fine trumpet player, again in the irrepressible mold of Armstrong; what was more, he wrote Benny Goodman's perennial swing smash "Sing, Sing, Sing." Prima's impact on popular culture was also significant; his pronounced ethnicity made it safe for other Italian-American singers to acknowledge their roots, and he was the first high-profile musical act to take up regular residence in the lounges and casinos of Las Vegas, helping to start the city's transformation into a broader-based entertainment capital. His musical legacy proved long-lasting, as covers of his classics became modern-day hits for David Lee Roth and Brian Setzer; additionally, the '90s swing revival, which sought to re-emphasize the danceability and sense of fun that had largely disappeared from jazz, brought Prima's music back into the limelight (as well as the good graces of critics).

Louis Prima was born December 7, 1911 in New Orleans, LA, to an Italian family who'd emigrated to the U.S. by way of Argentina. He took violin lessons as a youth, but switched to trumpet at age 15 when his older brother went out on tour with a band and left a spare instrument behind. By 17, Prima was playing professionally at a New Orleans theater, influenced chiefly by Louis Armstrong and King Oliver. This was a problem, since the theater was not a jazz venue, and Prima was fired. In the early '30s, he caught on with cornetist Red Nichols for a time, and moved to New York in 1934 at the urging of star bandleader Guy Lombardo, who had been impressed with Prima's trumpet playing. Initially struggling to find work, Prima formed a Dixieland-style backing group called the New Orleans Gang and landed a regular gig at a 52nd Street club known as the Famous Door. The band was a hit, adopting "Way Down Yonder in New Orleans" as their signature song, and recorded numerous sides for a succession of labels up through 1939; some of the better-known members included -- at various points -- clarinetist Pee Wee Russell, pianist Claude Thornhill, guitarist George Van Eps, reedman Eddie Miller, and trombonist George Brunies. Prima also traveled to Los Angeles periodically, and made cameo appearances in several Hollywood musicals, starting with the Bing Crosby Western Rhythm on the Range in 1936.

Meanwhile, Prima was composing original material, and in 1937 he completed a song called "Sing, Sing, Sing." Benny Goodman recorded an instrumental version and had a huge smash with it the following year, spotlighting it in his legendary Carnegie Hall appearance; to this day it remains one of the most readily identifiable melodies of the swing era. Prima broke up the New Orleans Gang in 1939 to form his own big band, which he dubbed the Gleeby Rhythm Orchestra. Following World War II, the band started to take off, landing hits with novelty numbers that often drew upon Prima's Italian background and accent. The first was 1944's "Angelina," a major success that paved the way for titles like "Felicia No Capicia," "Bacciagaloop (Makes Love on the Stoop)," "Please No Squeeza Da Banana," and "Josephina, Please No Leana on the Bell." Prima also made the Hit Parade Top Ten with songs like "Robin Hood" (1944; covered the next year by Les Brown for a bigger hit), "Bell Bottom Trousers" (sung by Lily Ann Carol in 1945), and "Civilization (Bongo, Bongo, Bongo)" (1947). He also wrote Jo Stafford's 1947 hit "A Sunday Kind of Love."}

In 1948, Prima hired a new female vocalist for his band, a 16-year-old Norfolk, Virginia native named Dorothy Keely, who was renamed Keely Smith. Prima parlayed her initial shyness into a stage routine where he attempted to break down her icily reserved façade. The contrast in their styles made for immediate chemistry, and Smith's boyish haircut only added to the duo's distinctive stage presence. Prima broke up the big band in 1949, and continued to work with Smith as a more streamlined nightclub act. They scored a hit in 1950 with their co-composition "Oh Babe!" and toured the country over the next few years. In the summer of 1953, Smith became Prima's fourth wife.

By late 1954, Prima was finding bookings harder and harder to come by. He talked a friend into booking him for an extended stay at the Sahara Hotel in Las Vegas, and while passing through New Orleans, he recruited locally popular tenor saxophonist Sam Butera as a possible collaborator if things went well. They did, and Prima called Butera out to Vegas, asking him to bring a few more musicians; the new group debuted at the Sahara on the day after Christmas, and Butera dubbed them the Witnesses during Prima's first on-stage introduction. Their act quickly became a sensation around Las Vegas, and their engagement turned into a residency, billed as "The Wildest Show in Vegas," which ran up to five times a night. Prima and Smith's comic banter was riddled with sexual innuendo, and they sometimes rewrote the lyrics to popular standards in the same spirit; meanwhile, Butera's jump blues/R&B background kept the music equally lively. Even if the music was aimed at older listeners, it shared a great deal of the spirit of early rock & roll.

In 1956, Prima inked a new deal with Capitol, which marked the beginning of the most celebrated and influential period of his recording career. His first album for the label was 1956's The Wildest!, which successfully translated the high energy of his live act into a studio recording; it featured many of his best-known latter-day songs, including the "Just a Gigolo/I Ain't Got Nobody" medley, "Jump, Jive an' Wail," "Buona Sera," "Oh Marie," and the jive-talking duet "The Lip." Over the next few years, Capitol issued six more Prima albums, highlighted by 1957's The Call of the Wildest and 1958's concert set The Wildest Show in Tahoe. He appeared frequently on The Ed Sullivan Show and other variety programs, and in 1958 he and Smith won a Grammy for their hit version of "That Old Black Magic." In 1959, they appeared in the film Hey Boy! Hey Girl!, which featured their renditions of the title song, "Lazy River," and "Banana Split for My Baby," among others.

While Prima and Smith boasted terrific chemistry on stage, their infidelity-riddled marriage was floundering by the close of the '50s. In 1961, Prima switched from Capitol to Dot Records, and from the Sahara Hotel to the Desert Inn; with his popularity still running high, both deals netted huge sums of money. However, Smith divorced him later that year, scuttling the act and largely negating the deals. Prima returned to Capitol for one final album, 1962's The Wildest Comes Home, and hired a new female vocalist, Gia Maione, who became his fifth wife in 1963. Without Smith, he was never again as popular or prolific on record, but he continued to perform in Las Vegas with Butera and the Witnesses, and toured successfully as well. In 1967, Disney tapped Prima to voice the character of King Louie, ruler of the orangutans, in its animated adaptation of The Jungle Book; his featured number, the swinging "I Wanna Be Like You," ranks among the best-loved Disney songs of its era.

Prima spent much of the late '60s and early '70s playing Vegas casinos and lounges, most notably at the Sands Hotel. With more and more musical acts taking up residence in the city, Prima no longer had the drawing power of old, and in the early '70s he and Butera returned home to New Orleans, where they made a steadier living playing in the French Quarter for the tourist crowd. In late 1975, Prima underwent surgery to remove a brain tumor, and fell into a coma; although he survived for nearly three more years, he never regained consciousness, and died on August 24, 1978. Prima's music began to reappear in subsequent years; ex-Van Halen singer David Lee Roth scored the best-remembered hit of his solo career with a carbon-copy version of "Just a Gigolo/I Ain't Got Nobody" in 1985, and onetime Stray Cat Brian Setzer scored a Grammy-winning hit with his cover of "Jump, Jive an' Wail." Prima's original version was featured in a Gap commercial around the same time, and the swing-dancing fad of the time helped bring the rest of his music back into the public eye. Meanwhile, Sam Butera continued to perform Prima hits from the golden years on the casino circuits in Las Vegas and Atlantic City