Doug Shorts has been trying to get his foot in the door of the music industry since the late 60s, when he was a student at Wells High School near Ashland and Augusta. But it wasn't until about five years ago, when he working as a doorman on Lake Shore Drive, that he met the man who'd finally release some of his songs on a proper label. Shorts, 62, lives in Chatham, but he grew up on the near north side, where he started singing in soul bands at age 16. For decades his career in music was a collection of almosts­. In the early 70s he almost joined Chess Records vocal-soul group Shades of Brown while touring as their support act; a few years later he almost released four songs he'd cut with future Prince producer David Z.; in the late 70s he almost finished a recording session for Brunswick Records; in the mid-80s he almost signed a songwriting contract with Motown.

In May 2012, though, local funk and R&B label Cherries Records most definitely released a Doug Shorts single: "Feels So Right" b/w "Love's Gone Wrong," whose smooth, contemporary funk backdrops come from producer Cermakk, aka Cherries cofounder Andrew Brearley. On Tuesday, July 2, Cherries will drop a second Shorts seven-inch, the silky "Don't Sleep on My Love" b/w "Bet I'll Know the Next Time," and on July 26 they'll celebrate by debuting a video at the Whistler. So far these two records are his only proper releases, but that's about to change in a big way.

The only previous fruits of Shorts's efforts have been a handful of recordings that he put out himself or paid to release on vanity labels. None of them sold, but they didn't all disappear. A single called "Something to Be Done" b/w "You," which Shorts recorded with his 70s band the Master Plan Inc., ended up in the hands of Chicago soul expert Bob Abrahamian in April 2009. "No collectors had known or seen this record," says Abrahamian, who hosts the WHPK show Sitting in the Park. "I was like, 'What the hell is this?'" Abrahamian found several copies of "Something to Be Done" while visiting Herb Butler, who'd been a member of a contemporaneous group called the Players, and he asked to take a copy. "When I got home and played it I was like, 'Wow, this is really good.'" He's not the only one who thinks so: in 2011 a collector sold a copy online for $1,000.

Only Abrahamian and other diehard collectors might ever have heard Shorts sing, because he'd all but given up on music in the early aughts—it was a chance encounter with Galapagos4 rapper Brian "Robust" Kuptzin about five years ago that turned him around. At the time Shorts was the night doorman at the condo on Lake Shore Drive and Irving Park where Kuptzin's girlfriend lived. Kuptzin introduced Shorts to Brearley, who'd been a producer for Galapagos4 under the name Meaty Ogre since 2000. Brearley is also a record buyer and Chicago soul fan, and in 2012 he and his wife, Sheila Hernando (aka DJ Shred One), would launch Cherries.

Brearley and Hernando have been among Shorts's biggest boosters, but Cherries isn't the only operation with a stake in Shorts's music. UK label Jazzman will release a Master Plan compilation in September, the Numero Group has a pair of Master Plan seven-inches due in the fall, and late this year rap producer Frank Dukes (Ghostface Killah, Danny Brown, Tree) and Dap-Kings drummer Homer Steinweiss hope to put out an album they cut with Shorts in 2012, tentatively titled Silver & Gold Featuring Doug Shorts. "Nothing happened forever," Shorts says. "Then all of a sudden people coming at me from all angles."

Frederick Douglass Shorts (his father named him after the abolitionist) was born in 1951 and grew up just outside Cabrini-Green, where he lived with his mother, Juanita, her six brothers, and his maternal grandparents. His uncles would often sing popular doo-wop tunes around the house. "They sang the best harmonies ever," he says.

The first group among many that Shorts would join was called the Mannequins; he even dropped out of high school to sing with a Kansas City act called the Visitors. (He wouldn't get his diploma till 1977.) He quit after they persuaded him to come to Kansas City, then played just two gigs in two months. Soon he was so discouraged he nearly dropped out of music. In 1970 one of Shorts's collaborators, guitarist Joe Stevenson, convinced him to hit the road with Shades of Brown, in whose backing band he was playing. Shorts started as their driver, but impressed them with his singing and graduated to opening their shows—an arrangement that lasted about a year, till one of Shades of Brown's singers left to marry a woman in Kalamazoo. The group's producer suggested Shorts for the vacant spot, but they disbanded instead.

In the early 70s, Shorts started the Master Plan with Stevenson, drummer Dean Knox (from Shorts's earlier band the James Clark Revue), and bassist Eddie Manning (from the Mannequins' closest rivals, the Fugitives). The Master Plan changed lineups, broke up, and re-formed several times before calling it quits in 1980, but the group's core turned out to be Shorts, Knox, and the Fugitives' Archie Brooks on vocals and guitar.

Shorts initially saw Brooks as potential competition, but the two ended up long-term writing partners—they still work together today. "He was like the cat to look up to, the way he carried himself—he dressed nice, and people liked him," Brooks says. They collaborated on the Master Plan's songs and, along with Knox, went to a sixth-month business-school program in 1974—after which they incorporated their band, changing its name to "the Master Plan Inc."

The Master Plan Inc. gigged around the midwest and Canada, and in 1975 they recorded four songs in Minneapolis with engineer David Rivkin (aka David Z.), who would later achieve a strange kind of fame as a producer for Prince. The band didn't have enough money to pay for their masters at first, and when Shorts went back to retrieve them a couple months later, he ended up stranded in Black River Falls, Wisconsin, without the tapes—he'd left them (and his winter coat) on a Greyhound bus during a rest stop, and the driver had pulled away without him.

Fortunately Shorts caught the next bus and recovered everything from the lost and found in the Chicago station. Later he took the four songs to a local studio to do more work on the mixes with engineer Ed Cody, who worked with a huge number of soul groups in the 60s and 70s; during the sessions Cody made a submaster copy for himself.

That was pretty much the end of the road for those tunes, though—like the songs that the Master Plan recorded with Brunswick in the late 70s, they didn't get released. The Brunswick deal, such as it was, came about via Gary Jackson, who cowrote Jackie Wilson's "(Your Love Keeps Lifting Me) Higher and Higher." He worked at Brunswick, and he'd managed Shorts's band for about a year before offering them a verbal contract. The label's reputation was tanking at that point, though: in 1976 several Brunswick executives were charged with fraud and conspiracy, and by the time the case was thrown out on a mistrial in '78, the label was crippled. "Everybody knew that everybody at Brunswick were crooks," Shorts says. "He was one of them, so I figured we'd be OK cause our manager is one of the crooks. As long as he cool with us, we all right. So we went on that premise that we could trust Gary, so we didn't sign anything—we just went in and started recording."

Things went sour after Brunswick house producers started horning in on the Master Plan's sessions. Shorts says he confronted label head Raymond Haley and was told that nobody makes money from their first release—that is, the band shouldn't expect to see any of the potential profit from their recordings. The Master Plan backed out on Brunswick, then left without their masters (though Shorts had a copy of the unfinished songs on quarter-inch tape). Shorts says Haley was none too pleased to pay for the band's studio time without any records to sell, and the two of them almost came to blows.

"I told him, 'Hey man, you might kick my ass, but you not gonna come out of it without a scratch,'" Shorts says. "He thought better of that one, and he left me alone. After that I thought to myself, 'Well, I better go out and learn how to fight, because I'm gonna get into this situation again—I'm not gonna quit music because of these people.'" At Brooks's recommendation, he took up karate; he's now a fifth-degree black belt, and teaches twice a week at the Wabash YMCA.

Within a few months, Shorts funded a new Master Plan session with Cody; in 1980 he self-released the resulting single, "Something to Be Done," on the vanity label Mundo. He hand-delivered it to a few stores before giving up, discouraged because he couldn't afford to promote it. In 1984 the seven-inch "How Slick Is Slick," which he self-released under the name Doug Shorts & the Master Plan Band, met the same fate.

In the mid-80s the Motown label began courting one of Shorts's collaborators, Roosevelt Purifoy, impressed by his production work on a record by Vanessa Holmes & Chicago Nite Life called "Take My Love." Shorts saw an opportunity: he put a group together with Purifoy and Brooks, and in 1986 he plotted a trip to Motown's Los Angeles offices. Unfortunately, he was the only one who went. Purifoy couldn't get to LA. "I don't fly," he says. "It's kind of hindered me in a lot of areas." Purifoy missed out on his chance for a Motown deal, and because he didn't show, Shorts didn't get a shot at a songwriting contract—an especially bitter disappointment because he'd turned down a similar offer from Motown in order to work with Brunswick in the late 70s.

"I was so embarrassed that I'd liquidated and told everyone 'I'm going to LA' that I was stuck in LA," Shorts says. He worked odd jobs—dishwasher, parking manager, head of security at Buccellati jewelry in Beverly Hills, even TV and movie extra. (Shorts says he's appeared on NYPD Blue, Beverly Hills 90210, Family Matters, and ER, and you can spot him dancing in a pink sport coat during the opening credits of the 1998 Adam Sandler movie The Wedding Singer.) From time to time he still recorded music; he self-released a cassette called Master Plan in Progression in 1990 and a gospel CD called Praises in the early aughts. Neither went anywhere, and music stayed on the back burner. Shorts had already thrown away all his old master tapes and most of his own records, not long after ending up in LA—he'd stored them in his mother's basement, and got rid of them on a visit in the late 80s. "I decided, 'Why should I litter my mom's house with this crap?'" he says. "The garbage truck was coming, and I just went and dumped it outside."

Shorts and his mother are close, and she's the reason he moved back to Chicago in 2003. "I said, 'I should be there with her, have coffee with her in the morning and stuff instead of being selfish and being by myself,'" he says. "I did a lot of soul searching, 'cause I know I didn't want to come back to Chicago, but the fact is she's getting old. I wanted to spend the twilight years with her." Shorts moved into the attic at his mother's house in Chatham, where she's been living since 1974, and set up a modest studio in the basement, which he calls Funkland. He got a security job at the Ginger Ridge Apartments in Calumet City, then moved on to the doorman post at the Lake Shore Drive condo where he met Kuptzin.

Kuptzin says Shorts was always friendly, but they bonded after Kuptzin walked in one night reeking of weed. Shorts noticed: "He said, 'I like that cologne,'" Kuptzin recalls. Shorts had a boom box at work and would occasionally play his favorite old soul music (including some of his own material), which caught Kuptzin's ear—he mentioned to Shorts that he knew some record dealers who were into that kind of stuff. Andrew Brearley was one of them.

At the time Brearley was living in Phoenix—he'd moved there in 2008 with his wife and their son, Eleazar, and founded a streetwear and record store called Grandiose. The shop only stayed open for nine months, and shortly after it closed Brearley got divorced. He and Hernando started dating in 2009—she lived in San Francisco, but they'd met when she visited the shop on a trip to Phoenix—and at the end of July 2010 the new couple and Brearley's son moved to Chicago.

Just days after arriving, Brearley went vinyl hunting at the Record Dugout near 63rd and Austin, and a peculiar seven-inch caught his eye—Doug Shorts's "How Slick Is Slick." He didn't know the name, but he bought it anyway. The next day Kuptzin dropped by and mentioned the soul-loving doorman he'd befriended. "He's like, 'Man, you need to hook up with my boy Doug Shorts," Brearley says. "The record was literally right there, and I just grabbed it and he's like, 'Doug Shorts?' His face went white."

Kuptzin put them in touch, and Shorts played Brearley his old recordings. "He was playing me stuff off of DAT and third-­generation recordings from cassettes," Brearley says, "but the material itself was amazing shit. I was like, 'Man, we gotta get this out.'"

Brearley referred Shorts to Abrahamian, who interviewed him on Sitting in the Park in May 2011 and played some of those old recordings, including a muddy version of a breezily brassy unreleased tune called "Try It You'll Like It." A friend of Brearley's passed Shorts's music along to the folks at Daptone Records, who took about a year to decline to release it—they liked what they heard, but the recording quality was too poor.

Dap-Kings drummer Homer Steinweiss heard the music at Daptone, though, and he reached out to Shorts about a modern-soul project he'd been working on with rap producer Frank Dukes. They'd tried working with a few singers, but Shorts was the first who clicked; they flew him to Brooklyn last summer and recorded Silver & Gold Featuring Doug Shorts in five days. "He was just super smooth with it," Dukes says. "His vocals are just silky, man."

By that time Brearley and Hernando had launched Cherries by releasing Brearley's collaboration with Shorts. Brearley had made about 40 modern funk beats for his Cermakk project, and he passed some along. "He was like, 'Yeah, I can do something with this,'" Brearley says. Hernando claims the label sold all 300 copies in five days.

In late summer 2012 Brearley got a call from Record Dugout owner Steve Batinich, who had several boxes of unmarked tapes from the widow of a Dugout regular named Joe Lopez. "I was like, 'You gotta sell it to Numero Group,'" Brearley says. "They're the only ones that are gonna do the right thing with it."

Lopez had bragged about owning tapes from Ed Cody's collection, which seemed unlikely given Cody's reclusiveness—but he'd been telling the truth, and the Numero folks sorted through the stash and bought boxes of tapes they were reasonably sure had belonged to the producer. Numero's Rob Sevier occasionally checked in with Abrahamian for help identifying new discoveries, and in February of this year he got a startled reply. "I responded with, 'Holy shit, this is the unreleased 'Try It You'll Like It,''" Abrahamian says—the song he'd played from Shorts's deteriorating tapes on his show almost two years earlier.

It was one of four Master Plan songs Numero found that month—Cody's submaster copy of the remixed David Z. session—and the label plans to re­issue all of them in the fall. Jazzman began assembling its 18-track Master Plan compilation before this find, relying mostly on Shorts's lower-quality copies and some acetates he found in his mother's attic.

Brearley and Hernando are moving to New York in August to take new record-buying jobs, which should give them the financial stability to expand Cherries. They're hoping to do more releases, start an in-house band, and tour. They also want to keep collaborating with Shorts—and he hopes to hit the road too, once more of his music is out there. So far he's only performed live three times in the past two years. "We're shooting to go from here on out and hopefully do a lot more, if Doug doesn't get too big for us," Brearley says.

"Nah, I ain't goin' nowhere," Shorts says. "I'm sticking with the Cherries."