When You’re Smiling: Louis Armstrong’s Sunny Side of the Street

“I’ve seen everything from a child, coming up,” Louis Armstrong once said. “Nothing I ain’t never seen before.”

He wasn’t kidding. In his revelatory 1954 memoir, Satchmo: My Life in New Orleans, the legendary entertainer recounts his hardscrabble childhood in “disgustingly segregated and prejudiced” New Orleans. Armstrong doesn’t sugar coat the realities of his early life—digging through trash cans outside restaurants to find food he could sell, surviving the violence and chaos that surrounded him.

But it is the pioneering jazz genius’s overwhelming empathy and humor that make this autobiography a must-read. With what writer Dan Morgenstern (in Terry Teachout’s definitive biography Pops: A Life of Louis Armstrong,) calls Armstrong’s “ceaseless fascination with the foibles of human beings,” he vividly paints a picture of the eccentrics who populated turn-of-the century New Orleans. Constantly looking for the good in everyone, for tender mercies and acts of kindness, Armstrong celebrates the sort of generosity he’d eventually be famous for.

A sensible perfectionist, Armstrong would take New Orleans, and the lessons it taught him, to stages and screens around the world. “When I pick up that horn, that’s all,” he once said. “The world’s behind me, and I don’t feel no different about that horn now than I did when I was playing in New Orleans. That’s my living and my life. I love them notes. That’s why I try to make them right.”

Little Louis

“Mayann told me that the night I was born there was a great big shooting scrape in the Alley and two big guys killed each other,” Armstrong writes in Satchmo: My Life in New Orleans.

Until the day he died, Louis Daniel Armstrong believed he was born on July 4^th, 1900. But according to Teachout, he was actually born on August 4, 1901, to William Armstrong and a 15-year-old Mary Ann Albert (whom Armstrong called Mayann).

Armstrong was raised by his beloved paternal grandmother, Josephine, in a New Orleans ward teaming with mayhem and music. “There were churchpeople, gamblers, hustlers, cheap pimps, thieves, prostitutes, and lots of children,” he writes. “There were bars, honky-tonks and saloons, and lots of women walking the streets for tricks to take to their ‘pads’ as they called their rooms.”

The people-pleasing child, proudly wearing his white Little Lord Fauntleroy suit, would move to an even tougher part of town with Mayann and her sister, Mama Lucy, when he was five. Armstrong’s love for the hard-drinking, humorous, big-hearted Mayann (whom Teachout believes was occasionally a sex worker) and the values she instilled in him radiate from every page.

“Whether my mother did any hustling, I cannot say,” Armstrong writes. “If she did, she certainly kept it out of my sight. One thing is certain; everybody from the churchfolks to the lowest roughneck treated her with the greatest respect. She was glad to say hello to everybody and she always held her head up.”

Armstrong held his own head up even when he roamed barefoot through the streets, looked after by an extended community, and soaking in everything he saw and heard. The famed Funky Butt Hall was on the corner where he lived, and though Armstrong was not allowed in, he became enamored with the revolutionary blues and jazz that was percolating within as he listened from the sidewalk. “As I grew up,” he writes, “I observed everything and everybody. I loved all those people and they loved me. The good ones and the bad ones all thought Little Louis (as they called me) was OK.”

Silver Lining

At only eleven years old, Armstrong was selling newspapers and singing in a quartet in the fabled red-light district of Storyville. “Singing at random,” he writes, “we wandered through the street until someone called to us to sing a few songs. Afterwards we would pass our hats and at the end of the night we would divvy up.”

One New Year’s Eve, the quartet was working the neighborhood when a man shot a gun in the air to celebrate. To the delight of his bandmates, Armstrong pulled out one of his “stepfather’s” guns and joyously began firing in the air as well. He was nabbed by a cop and taken to jail.

Armstrong’s account of the arrest is one of the most devastating and infuriating passages in Satchmo. He recalls crying and begging for his mother, only to be thrown in a wagon and sent to the Colored Waif’s Home for Boys, a reform school. As Teachout notes, Armstrong seems to have been constantly looking for a father figure, and gravitated towards a Black music teacher named Peter Davis. Initially, he feared that Davis thought that “since I had been raised in such bad company, I must also be worthless.”

A diligent Armstrong went to work at winning Davis over. “I would catch his eye meeting with mine,” he recalls. “I would turn away, but he would catch them again and give me a slight smile of approval which would make me feel good inside.”

Davis eventually invited him to join the school’s band, and quickly discovered his student was a musical prodigy. Armstrong took great pride in being made the home’s bugler, and was thrilled when Davis gave him a coronet and taught him how to play it. He was soon the most popular boy in school, and the band’s leader. One day, they paraded through Armstrong’s neighborhood, where he got a hero’s welcome:

Everybody was gathered on the sidewalks to see us pass. All the whores, pimps, gamblers, thieves and beggars were waiting for the band because they knew Dipper, Mayanns’s son, would be in it. But they never dreamed that I would be playing the coronet, blowing it as good as I did… They asked Mr. Davis if they could give me some money…those sports gave me so much that I had to borrow the hats of several other boys to hold it all.

Dixieland Delight

“Jazz and I grew up side by side,” Armstrong told Time Magazine in 1949.

A nostalgic love letter to his hometown’s musical legacy, Satchmo prompts readers to share in Armstrong’s joy after he is released from reform school at 14 and almost immediately gets a job at a hard-edged honky-tonk. Soon, he’s blowing his coronet and learning from jazz greats and pioneers like Kid Ory and his hero Joe “King” Oliver, a gruff coronet innovator who took Armstrong under his wing.

“I used to hear some [of] the finest music in the world listening to the barroom quartets who hung around saloons with a cold can of beer in their hands, singing up a breeze while they passed the can around,” he writes. “I thought I was really somebody when I got so I could hang around with those fellows—singing and drinking out of the can with them.”

Music permeated every corner of New Orleans: parades, picnics, honky-tonks, brothels, churches. Even his boss for a time, Lorenzo the Junk Man, worked with an old tin horn. “He could actually play a tune on it, and with feeling too,” Armstrong writes. “It used to knock me out to hear him play a real tune to call people out of their houses and backyards.”

And then there were the city’s legendary funerals, where Armstrong would frequently play for extra cash and describes in sparkling detail:

After the brother was six feet underground the band would strike up one of those good old tunes like ‘Didn’t He Ramble’ and all the people would leave their worries behind. Once the band starts, everybody starts swaying from one side of the street to the other, especially those who drop in and follow the ones who have been to the funeral. These people are known as the “second line” and they may be anyone passing along the street who wants to hear the music. The spirit hits them and they follow along to see what’s happening.

He would also participate in musical tailgates, where competing bands would face off against each other in wagons, with Joe Oliver always making sure to let Armstrong have his time to shine. Spurred by competition and comradery, they would “give with that good mad music they had under their belts and the crowd would go wild.”

Nobody Knows the Trouble I’ve Seen

Speaking of musicians who shaped him, Armstrong writes, “Lot of them were characters, and when I say ‘characters’ I mean characters!”

Armstrong lovingly name checks them all, as well as the other folks who fascinated him as a youth.

There were Cocaine Buddy, Mary Jack the Bear, Shot Madison, One Eyed Bud, Big Nose Sidney, Redhead Happy Bolden, Sore Dick, Sweet Child, Little Head, and Lulu White, the most magnificent Madam in Storyville. With a sensitivity rare for a big star, he nostalgically sketches each person, making them come alive with humor and empathy.

After a brief interlude as a failed pimp (one of the most darkly humorous stories in the book), Armstrong found a day job driving a coal cart through Storyville, while playing music at night. With the money he earned, he supported his family, along with his cousin Clarence, who Armstrong adopted when he was still a teen.

The going was shockingly rough. Armstrong recounts shootouts at clubs, countless knife fights between sex workers, domestic violence, and his tumultuous first marriage to Daisy, a sex worker with a violent temper. He kept playing after one shoot-out, even as patrons attacked the stage. “Bottles would come flying over the bandstand like crazy…but somehow all that jive didn’t faze me at all, I was so happy to have some place to blow my horn.”

By the early 1920s, Armstrong was the hottest coronet player in town (he would not switch to the trumpet till the mid-1920s). He learned from his mentors’ mistakes and became pragmatic about his dreams. “I’ll never be rich,” he writes. “But I’ll be a fat man.”

You Can’t Go Home Again

Unfortunately for us, Satchmo: My Life in New Orleans ends in 1922, when he is called up to Chicago to play with his hero Joe Oliver. “I had hit the big time,” he writes, ending this perfect little memoir. “I was up North with the greats. I was playing with my idol, the King Joe Oliver. My boyhood dream had come true at last.”

By the early 1930s, Armstrong—with the help of his savvy second wife, Lil Hardin—was being hailed as a musical genius and playing endless tour dates. But he still saw his share of trouble and was briefly on the lam from the mob, later remembering Al Capone as a “nice little cute fat boy.”

Armstrong also faced horrific prejudice. While traveling in Memphis in 1931, he and his bandmates were arrested on nonsense charges. According to Teachout, they were released only when Armstrong agreed to play a benefit concert for the force. On a live broadcast of the benefit that night, Armstrong stepped up to the mic. “I’m now going to dedicate this tune to the Memphis Police Force: ‘I’ll be glad when you’re dead, you rascal you.’”

Forever on the road, Armstrong would find his first real home since he left New Orleans when he married his fourth wife, Lucille Wilson, in 1942. “It dawned on me that our lives were practically the same,” Armstrong wrote, per Teachout. “Good common sense—great observers…we were not particular about phony people, etc.—what we didn’t have we did without.”

Lucille was also as thoughtful as her husband. Knowing Armstrong had never had a Christmas tree as a child, she set one up in their hotel room on their first Christmas together. Armstrong was transfixed. “We finally went to bed,” she later recalled. “And Louis was still laying in the bed watching the tree, his eyes just like a baby’s eyes would watch something…I said, ‘Well I’ll turn the lights out now on the tree.’ He said ’No, don’t turn them out. I just have to keep looking at it.’”

What a Wonderful World

By the 1950s, “Ambassador Satch” was a worldwide icon, touring with his All-Star Band, making albums with Ella Fitzgerald and starring in Hollywood films like High Society. But he was also heavily criticized by a new generation of jazz musicians and artists like Dizzy Gillespie and Miles Davis, who saw him as a sellout who mugged for white audiences.

Armstrong did speak out in 1957, when President Eisenhower refused to insist that the Arkansas Little Rock Central High School integrate. As an unofficial goodwill ambassador for the State Department, Armstrong publicly called out the president, stating he was “two-faced” and had “no guts.” When Eisenhower finally did what was right, Armstrong sent him a telegram which read: “Daddy, You have a good heart.”

Armstrong’s big heart was often in evidence. He played music with the neighborhood children in Corona, Queens, where he and Lucille settled (living in what is now the Louis Armstrong House Museum). After shows, he would sit in his underwear and receive everyone from nuns to gangsters in his dressing room. He became known for his generosity, often slipping money to anyone who would ask. “Pops, I know they just taking me,” he told a friend, per Teachout. “But what can I do?...Poor bastards. They think they’re fooling me. But it’s all right.”

Armstrong admitted he was no “plaster saint.” He had an explosive temper and a wandering eye (his longtime mistress gave birth to his daughter, Sharon, in 1955). He obsessively taped his life, recording everything from fights with Lucille to jokes he had written and unvarnished, raw conversations about racism.

Luckily for us, Armstrong also wrote obsessively—“a two-fingered blip on my portable typewriter,” he joked. He wrote magazine articles; thoughtful, vivid letters to fans; reminiscences; and even started a book promoting the legalization of marijuana. Many of these are collected in the delightful compilation: Louis Armstrong: In His Own Words.

They are evidence of a life well lived. “My whole life has been happiness,” Armstrong recounted shortly before his death in 1971. “Through all the misfortunes…I did not plan anything. Life was there for me and I accepted it. And life, whatever came out, has been beautiful to me.”