Sometime in May, the 78-year-old jazz singer realized that his bed at Illinois Masonic Medical Center would be his deathbed. Shortly after retiring from his day job as a doorman at a north-side condo building this past winter, he had suffered a heart attack and slipped into a coma. He’d eventually regained consciousness, but he knew his weakened body couldn’t fight the pneumonia and diabetes much longer. So Steve Trimble called his niece, 73-year-old Helen Rathel, to his side and told her the kind of funeral he wanted.

“I want it to jam,” he whispered.

Trimble was virtually unknown outside a small group of south-side jazz musicians and aficionados–but within that circle he was beloved. The funeral was held on Friday, May 17, at Saint Stephen’s Evangelical Lutheran Church at 8500 S. Maryland. After an eclectic service that included a Buddhist ceremony and traditional Christian rites, Trimble got his wish: a jam session right there in front of the altar. Drums, bass, piano, and horn section stayed put for three hours while vocalists rotated in and out; the pastor put a stop to the New Orleans-style obsequies around 11 PM. Even without a death notice or obituary in any Chicago newspaper, more than 300 people showed up and signed a condolences book. Extra chairs blocked the aisles to accommodate the overflow.

Many of the musicians Trimble played with in his career attended the funeral but couldn’t stay for the jam session. Tenor saxophonist Sonny Seals, 71, and trombonist John Watson Sr., 65, were among them. “Sonny and I went,” Watson explained, “but we had to leave because we had a gig. That’s par for the course. I don’t think Steve would have minded.”

Seals and Watson are among the dozens of musicians Rathel has invited to play at a second memorial service for her uncle, to take place this Saturday, June 29, from 3 to 7 PM at the Soka Gakkai International Chicago Culture Center at 1455 S. Wabash. The public is encouraged to attend. Rathel isn’t sure exactly which musicians will show up; she just felt that after almost seven decades of living for music, Steve Trimble deserved a little more of it.

Trimble’s career began in earnest on July 5, 1939, when he and some childhood friends–including Jon Elroy Sanford, the boy who would become Redd Foxx–hopped a freight train bound for New York.

Trimble was born in Birmingham, Alabama, in 1923, the sixth of seven children, but shortly thereafter his family moved to Chicago, part of the Great Migration that brought African-Americans–and blues and jazz–to the north. As a young boy, Trimble heard jazz on the radio and fell in love. He competed in local talent shows, singing numbers by vocal groups like the Ink Spots and the Mills Brothers. In grammar school he sang and played the washtub bass (made from a metal tub, a two-by-four, and a string) in a street-corner band called the Four Bon Bons. While in high school, at DuSable, the Bon Bons–Trimble, Sanford, Pete Carter, and Lamont Ousley–performed for nickels and dimes. Convinced of their talent, the boys made their way to Manhattan; Trimble was just 16.

In Harlem, where they settled, the young men slept wrapped in newspapers. They turned to crime to make ends meet, mugging men at knifepoint and snatching women’s purses. And, just as they’d done in Chicago, they danced and sang on street corners and passed the hat. During one performance, according to Dempsey J. Travis’s 1999 biography The Life and Times of Redd Foxx, they were spied by a talent scout for Major Bowes’s Original Amateur Hour and appeared on the show, which was broadcast on CBS radio. The Four Bon Bons took second prize–a week’s engagement at the Apollo Theatre.

But soon their luck took a turn for the worse. Ousley and Sanford were sentenced to jail time after trying to run out on a restaurant bill. Trimble and Carter escaped, but that was the end of the Four Bon Bons. After getting out of jail Ousley joined the army. Carter returned to Chicago and lost touch with his friends. Sanford stayed in New York, changed his name to Redd Foxx, and became a legend.

Trimble also went back to Chicago, where, over the next six decades, he married three times and fathered two children. During World War II, classified 4F by the draft board, he worked in factories. Later he sold appliances at Polk Brothers. His last job, which he held for 19 years, was as a doorman at 2800 N. Lake Shore Drive, where I lived from 1993 to 1998.

Until just before his death, he continued performing, despite almost no hope of making it big. His evening didn’t always end when his shift did, at 11. Residents often saw him walking to his car wearing two-tone shoes, a white suit with padded shoulders, and a matching fedora.

Trimble’s various jobs paid the bills, but “he loved a microphone,” says Marion Burke, his longtime piano player. Beginning with the Four Bon Bons, he was in one band or another for most of his life. In the closing days of World War II, he played stand-up bass in the Sepia Tones. Though he claimed to be five-foot-four, he was at least two inches shorter than that, and the instrument towered over him.

The Sepia Tones traveled around the country in the mid-1940s and met with moderate success, Trimble told me in one of a series of interviews over the last seven months of his life. The group was winding down a stand in San Francisco and preparing for a gig in Los Angeles when disaster struck. They brought a couple women back to where they were staying in Oakland–“a black girl and a white girl,” Trimble said. “We were having a drink when the cops busted in on us. They busted us for running a house of prostitution on account of the white girl. We went to jail for that. There was a big to-do. That kind of messed up my plans to make the big time, just at the point when we were about to go over.”

While they were being held, they missed their date at the Florentine Gardens in Hollywood. “This would have been our big break,” Trimble lamented. “The group that worked in our place stayed there for a year. They were a harmony group just like us.”

In the 1950s he found a steady gig as the bass player with a band called Cats & the Fiddle that played on the chitlin circuit–a loose network of black nightclubs–mainly in Chicago. In the 1960s he formed the Steve Trimble Trio. He played bass and sang, Burke played piano, and Eddie Chappel played drums. They did club dates all over Chicago, and also weddings.

After his third marriage, to Mildred McClendon in 1972, Trimble began to cut back on gigs. But one night he didn’t give up was Von Freeman’s Tuesday-night jam session, which he still hosts every week at the New Apartment Lounge on East 75th. Freeman plays the first set with his band, then steps out of the spotlight to allow singers and other musicians to sit in. Trimble, always dressed in a natty suit, was a regular. He’d stroll in, order the “usual”–a white wine–and then wait to be called to the stage. He sang standards like “When You’re Smiling” and “East of the Sun.”

Freeman thought Trimble was a strong performer and compared him to another Depression-era DuSable graduate: Johnny Hartman. He especially liked Trimble’s way with a Louis Armstrong classic. “He did one of the most humorous versions of that Louis Armstrong song–what was it called?–‘Wonderful World.’ He’d tear up the house with that,” he says.

Trimble and Redd Foxx remained tight even as Foxx got famous. Whenever the star performed in the Chicago area at a theater without a house band, he hired Trimble to put together some musicians as an opening act, according to Seals, who was sometimes recruited to play tenor saxophone for these gigs. In the 70s, Trimble visited Foxx in California, and Foxx got him a small part on an episode of Sanford and Son–a nonspeaking role as a character in a gay bar. “Redd was trying to make a girl out of you,” Chappel razzed Trimble when he returned.

According to Trimble, Foxx encouraged him to move out west to give music a try in Los Angeles or Las Vegas. For reasons he didn’t understand himself, Trimble stayed in Chicago with his album of snapshots from the trip and a gorgeous electric stand-up bass, a gift from Foxx.

Over the years he accumulated quite a collection of friends better known than himself. Those relationships came in handy when, at the age of 74, he set about recording his first, and ultimately only, album: Keep on Smiling, a collection of pop and jazz standards in longish versions with generous solos. After Mildred died in 1997, Trimble decided to use money they had saved together to finance the recording. “I slowed down to an extent,” he said of the years they were married. “I didn’t press my music as much as I felt I should have. So I said to myself, ‘Why don’t you go all out for it this time, go all the way and try to record something?'”

For his band, he first secured Burke, the piano player from the Steve Trimble Trio. He also hired a powerful rhythm section: drummer William “Bugs” Cochran, who’d played with Sun Ra, and first-call bass player John Whitfield. The capper was getting Seals and Watson. Seals has played with everyone from Gene Ammons to Smokey Robinson; Watson played with Count Basie. “He’s got some of the best musicians from the south side on his album,” Freeman says.

The band recorded the album in one day, cutting every song in a single take, Trimble told me. It sounds as if it were recorded live at a very loose show in a 1940s lounge. Trimble’s baritone croon is weakened by age but still lively, and the players sound relaxed, subdued even. In his liner notes for the album, Larry Smith, the overnight host of Jazz Forum on WBEZ, wrote, “The feeling here is happy, relaxing and absorbing. This is one of the most relaxing sessions I’ve ever heard, a real comfort zone.”

Trimble sold copies before, during, and after performances; he also sold scores to residents of 2800 N. Lake Shore. In all, he estimated, he sold more than 1,000 CDs and cassettes at $15 apiece.

After the album was completed, the band that Trimble had assembled continued to play together. They had a regular gig on Wednesday nights at the Gold Post on East 75th. I saw a show last September. The lounge, on a street of vacant lots, charged a $5 cover. Inside it was decorated in late-20th-century Miller Lite, posters and mirrors with the brand logo on them covering the walls. The band was set up on the dance floor, which was small–the lounge itself was the size of a large living room, packed with about 80 people.

Trimble assured me the crowd was small. As usual he was dressed in an immaculate suit. He wore wire-framed glasses, and pomade coated his thinning hair. The microphone was malfunctioning, and he sat out a few numbers.

The crowd didn’t mind. They liked Trimble, but they loved Seals and Watson. During one extended solo, Watson took the spotlight first, moving all around as if chasing his slide trombone to keep it on his lips. The crowd cheered when he finished. As Seals embarked on a long solo of his own, Watson, wearing denim overalls and white sneakers, ran slowly in place. When Seals concluded, the crowd whooped and whistled and thumped on the tables. “When Sonny comes in,” Watson says, “the place goes up for grabs.” He says the band Trimble put together–which still plays together, as the Trimblers–is one of the last great bargains in entertainment. “You can’t get that kind of talent anymore for $5,” he says.

Trimble seemed to know what he had. “These guys are real hot tonight,” he said, agreeing with the crowd.

Some people think Trimble himself was the weak link. A former member of Freeman’s band characterizes him as a dilettante who some nights had trouble singing in the proper key. Week after week at Freeman’s jam sessions, he says, he watched Trimble drink two or three glasses of chablis, sing his same couple of songs, and call it a night. “It was his social life,” he says. “Von can make anyone look like a star.”

At 2800 N. Lake Shore, opinions of his singing were also mixed. His retirement party, held in February in the building’s 43rd-floor party room, drew more than 150 people. The line at the buffet table had a view of the Loop, and beer and wine were served.

Trimble was asked to sing a song. “OK,” he said, a smile expanding across his face.

“Twist his arm!” someone in the crowd joked.

Taking a microphone, Trimble said, “I thought you wouldn’t ask me.” He sang a cappella: “So long, I’ll hope we’ll meet again someday….” When he finished the tune, the crowd responded warmly.

“In that case, I’ll do another,” Trimble said, failing to notice the large contingent moving back toward the buffet table. “He’s serious,” I heard one resident say in dismay.

But Trimble also had numerous fans in the building. Cliff Wahlund, who identifies himself as a private investor, was one of them. He planned to finance Trimble’s second album, to be called “Another Side of Steve Trimble.” Trimble and Wahlund had chosen the tunes, among them “Blowin’ in the Wind,” “Something,” “Yesterday,” and “Danny Boy” as well as Sinatra’s “Talk of the Town” and Ray Charles’s “You Don’t Know Me.” Trimble had all of the same musicians lined up for the session. Seals and Watson were looking forward to it. “He was a great person, kind and wonderful,” Seals says. “He was an entertainer. His singing got better as the years went on, but as the years went on, his voice was going, so he became a better entertainer.”

Trimble never got around to making his second album. In March he played a gig with his band at Lee’s Unleaded Blues on South Chicago. (The band still plays Wednesdays there.) That night Trimble found himself winded by the cigarette smoke that hung like fog in the lounge. He sat out most of the act, and what few songs he did sing he performed sitting on a bar stool.

The next night he had the heart attack, and he spent most of the next two months in a hospital room. When I visited him at Illinois Masonic one morning, a toy statue with the word jazzman on its base sat on a table near the bed. The little jazzman would play a sax solo when you pushed a button. Trimble hardly seemed cheered by it, fretting about his last night at Lee’s. “In lounges, there is all this secondhand smoke, and there’s no ventilation in most of those places,” he said. “You can’t stop people from smoking. That’s part of the problem. I might have to stop altogether.”

Within a month he was dead–afraid, perhaps, to face life without a microphone.