Inside the making of Dessa's groundbreaking live album with Minnesota Orchestra

As she turned and gestured to her "band" late Tuesday night, Dessa finally acknowledged she was doing something never before attempted in Minnesota — something she thinks could only be done here, at least the way she did it.

The Minneapolis hip-hop star has made many albums before. She's already worked a lot with a big, unwieldy group of musicians that likes to lube up before a show.

But Dessa had never recorded an album involving a whopping 73 players, 1,500 sheets of music, librarians, a contrabassoon, a conductor, union-mandated rules, a strictly timed 60-minute "patch session" and 2,100 audience members.

"There's a reason most underground rappers don't get to record with an orchestra," she told the crowd at Orchestra Hall in Minneapolis. "It's a lot of work."

A lot of faith and quite a bit of Minnesota Nice also came into play as we followed Dessa and the Minnesota Orchestra through the making of their live recording last week — uncharted territory for all involved.

Orchestra subscription ticket holders rubbed dinner-jacketed elbows with Dessa fans in "No Kings" hoodies at the sold-out concerts Tuesday and Thursday recorded for an album due next fall on Dessa's homegrown record label, Doomtree Records.

Everybody seemed to love the idea that the Grammy-winning orchestra's recording projects this year include both Mahler's Tenth Symphony and a new indie-rap joint.

"If you don't believe this is a trailblazing orchestra, show me another that's recorded for a hip-hop label," bragged Sarah Hicks, principal conductor for the Live at Orchestra Hall series and baton-wielder for these performances.

It's not unprecedented for the hip-hop and classical worlds to come together.

Two of the most revered rappers in the game, Nas and Kendrick Lamar, recently did orchestral concerts at the Kennedy Center in Washington, D.C. (Coincidentally or not, Kennedy Center sent a programming scout to Dessa's concert Tuesday).

This also wasn't Dessa's first rodeo with the Minnesota Orchestra. She had performed with the big crew five times before, including two pairs of sold-out gigs in 2017 and 2018.

That no doubt helped sell the recording idea when Dessa pitched it last fall to the orchestra's top brass (executives, not players). While MN Orch doesn't worry as much about ticket sales as the many struggling orchestras out there, every orchestra is anxious to find new and especially younger audiences.

Just as important, the members genuinely like Dessa, according to Hicks.

The singer and rapper endeared herself last August when she accompanied the orchestra on its historic tour of South Africa, blogging about it for Minnesota Public Radio. She and her producer/arranger Andy Thompson also made good first impressions with their previous performances.

"They really collaborate with the orchestra, and don't just use it as sort of a backing band," Hicks said. "I truly believe we're doing something innovative here."

It certainly would be a new thing for Minnesota Orchestra to get a write-up from the Pitchfork music blog, or for Dessa to land coverage from the Classical Review. It's also new for the orchestra to make a record with any of its guest "pops" performers. Staff seemed eager to record other homegrown collaborations should this one succeed. (Paging the New Standards and Cloud Cult!)

"I'd love to think everybody who's buying every one of these Mahler recordings will also pick up Dessa's album with the orchestra," said Grant Meachum, director of Live at Orchestra Hall.

Here are snapshots from the complex and sometimes intense process of creating this historic recording.

Not counting all the work already done in translating/reinventing Dessa's music for her previous orchestra performances, the heavy lifting toward the live recording started back in mid-January.

That's when Dessa and her cohorts convened at Andy Thompson's basement studio in southwest Minneapolis to finish off "Grade School Games," a new song about life's big little moments intended just for the occasion.

"Part of the reason we're recording these shows is for all the people who couldn't make the earlier shows," she said. "But I also felt like I had to provide something fresh."

On this day, though, they were actually trying to ignore the big gigs coming in March.

"We're basically recording this one the way we would any other Dessa song," said Aaron "Lazerbeak" Mader, the longtime co-producer/beatmaker in Dessa's Doomtree crew. "Then we'll hand it over to Andy to work his magic."

Thompson, whom conductor Hicks calls "everybody's not-so-secret weapon," has arranged orchestral parts for Dan Wilson, Jeremy Messersmith, Cloud Cult, the New Standards, Scottish band Belle & Sebastian and even a song on Taylor Swift's "Red" album.

For the new track, he created string parts that he calls "robot strings," using a MIDI (computerized) keyboard.

"There's a lot of room there for more," Thompson said after a playback of the song, a statement that would prove very true come showtime.

In the interim, the secret weapon would write out hundreds of pages of new musical charts for "Grade School Games" as well as two older songs, "The Bullpen" and "Call Off Your Ghost," newly arranged for the live album.

Those charts were turned over in mid-February to the orchestra's library, which in castle-like fashion sits three flights of stairs above the hall and holds 100-some years' worth of sheet music.

There, Dessa's and Thompson's work was organized and divvied up to be sent out to musicians, who would have a few weeks to study it.

"With some of the pops concerts, it's just hours, and it's not nearly as thorough as what Andy gives us," raved assistant principal librarian Valerie Little.

Another reason hip-hop doesn't have the bad reputation here it has at other classical institutions.

Setup in Orchestra Hall started last Monday night. As Dessa and her co-vocalists played with different ear and stage monitors, Sarah Hicks came breezing in straight from the airport with the same excited gait as her small papillon dog, Pinkerton, who accompanied her to the stage.

"Let's do this," Hicks said.

While the sound within the hall was coolly, capably handled by audio engineer Jay Perlman — a veteran of First Avenue and other clubs in town — the sounds to be recorded onto a hard drive were a whole other issue.

Almost 60 microphones had to be wired up, including the handheld microphones used by Dessa and her singers: longtime confidant Aby Wolf (who also served as vocal arranger), Ashley DuBose, Cameron Kinghorn and Matthew Santos, all of them veteran R&B, rock and hip-hop vocalists.

"No more than three fingers away from your mouth," Perlman instructed. Any further, and the sprawling orchestra would bleed into the mics.

Chatting before the soundcheck, Dessa bristled at the idea that this project might water down the more volatile ingredients in hip-hop — or legitimize it in the eyes of anyone who looks down their nose at the genre.

"For the record: I didn't come up with the idea for conscious rap," she said. "I learned that from black men. I wouldn't want to accept a compliment like, 'She's cleaning up rap.' I'm making music I believe in, and I learned how to do that from those men making music that moved them."

Hicks used the time to go over charts with Dessa's drummer, Joey Van Phillips, who was recruited to help arrange percussion. Not surprisingly, rhythm is the trickiest part of adapting rap music into the classical realm, according to Hicks.

"He's really driving the groove," she explained. "There's a lot more give-and-take during that process than a typical orchestra performance — which our musicians actually enjoy."

What drummer wouldn't like playing breakbeats versus Bach?

The full band arrived Tuesday morning, day of show, for two hours and 30 minutes of rehearsal, with one 20-minute break. That's it. The times were set and strictly followed per the musicians' union, a far cry from Doomtree rehearsals of Dessa's yesteryears.

As the 69 orchestra musicians settled in behind her in street clothes — that much did recall a Doomtree rehearsal — Dessa didn't seem at all nervous. Instead, she looked incredibly determined.

With the multi-tasking skills that allowed her to release a solo album, a memoir and her own whiskey brand all just in 2018, the 37-year-old busybody alertly bounced from tweaking a four-part vocal arrangement to asking for a different volume for the strings in her in-ear monitor to popping open a can of LaCroix.

"Can I get a C from you?" Dessa asked a cellist, then went straight into singing the refrain ("Now the bough breaks") from her 2010 hit "The Chaconne."

Her manager, Becky Hoffmann, watched from the wings with Lazerbeak and Thompson. "Which of the arrangements are you most proud of?" she asked Thompson.

"Or: Which do you think could make the most money," Lazerbeak bluntly put it.

She wore the red cape again, the one that sparked a local media buzz after last year's orchestra shows. But she saved it till after intermission and only used it for a song or two, instead favoring a black leather one-piece romper à la Jane Fonda's "Barbarella" sci-fi warrior get-up.

That Dessa paid any mind to her attire seemed both impressive and beside the point, as did the alluring light and video backdrop for her two nearly hourlong sets Tuesday. This performance was to prove her music could stand up on its own in a hall where music is hallowed.

If gasps, swoons and whoops from the audience were any indication, it soared. The jittery beats in "Warsaw" and "Jumprope," two highlights from last year's studio album "Chime," were turned into dizzying vibrations by the small army of percussionists. The light, jazzy tones in "Dixon's Girl" — about a real-life encounter Dessa had with an abused woman at a gig in Jackson, Miss. — became a plush pillow of woodwinds and strings

Two of the night's heaviest tunes, "5 Out of 6" and "Fire Drills," were just plain slamming by any hip-hop fan's measure, with piled-on layers of urgency and rhythm that could double as the score for a big-budget action movie.

At one point, Dessa — who spent the past decade normalizing the phrase "female rapper" in the notoriously macho hip-hop world — pointed out another unique trait of this project: its feminine DNA makeup.

Besides the headliner, conductor and vocal arranger, all but one of the principal string players were women. So you could have bet your copy of Dessa's empowering 2018 memoir "My Own Devices" that feminism would also play a thematic role in the performance. There was even an homage to Ruth Bader Ginsburg.

During one of the few breaks in the action, Dessa gave a shout-out to the Target store two blocks away.

"I'm about 90 percent shapewear right now," she told the crowd.

Even wardrobe malfunctions were fended off in the week's thorough preparations.

Dessa's parents, bandmates and friends gathered in a private atrium for a little mutual afterglow. Two of the people who know her best, her mom and Wolf, confirmed what seemed impossible: Dessa was cool as beans that night, on stage and off, despite the daunting task at hand.

"I think it helped a lot that we'd been up on that stage before," said Wolf, "which, believe me, was overwhelming the first time."

Talk of how the recording went was mostly put on the back burner, so everyone could burn off a little steam. About an hour and two free drinks into the soiree, though, Lazerbeak thought to ask the Live at Orchestra Hall director a rather important question.

"Don't worry, it's safe and sound, locked up in my office," Meachum said of the hard drive that held the night's recordings.

In a conference room overlooking the Peavey Plaza construction zone, the deconstruction of Night 1 began Wednesday afternoon with a batch of sugarless chocolate that left a bad taste in everyone's mouth.

The music, however — pumping out through hi-fi speakers from Thompson's laptop — had everyone feeling good.

A few flubs were caught in playback: a prominent trumpet note that was off by a bar; a sluggish tempo at the start of one song; a sliding note by one singer. Nothing that was too worrisome, given they'd do it all again Thursday.

"[Expletive] is gonna happen, but it's very unlikely it's going to happen twice," Hicks confidently pledged.

The formally requested changes for Night 2 were hyper-picky: More viola in "Good Grief," and altering one note in Measure 112 of "Boy Crazy" that only Hicks seemed to hear. Tweaks were sent to the orchestra librarians so the charts could be updated for Thursday's show.

During a lull, Meachum excitedly passed along an e-mail from the box office: 61 percent of Tuesday's crowd was orchestra first-timers.

"That's a very exciting number for our people," Meachum confirmed.

Sixty percent is also roughly how much of the music recorded last week will wind up getting cut, counting duplicate tracks and a few songs that will be trimmed altogether to fit the album format. But that process will come later, as will mixing of the 60-some microphone feeds.

That this was far from a traditional orchestra recording was apparent when the discussion turned to how difficult it might be to clean out F-bombs for radio edits.

There was also talk about the following night's "patch" session. An extra hour with the orchestra (but without an audience) was scheduled after Thursday's show to re-do parts that needed fixing, or to record instrumental versions of songs for possible movie or TV use.

Again, strict union rules were in play. As the vice president of orchestra administration, Beth Kellar-Long, stressed the preciseness of the timing — 40 minutes for music, 20 for breaks — Dessa for once looked nervous.

"I could wear a clock around my neck like Flavor Flav," Hicks wryly suggested, referencing the hype man in the legendary rap group Public Enemy who always lets you know what time it is.

Dessa and Lazerbeak laughed hardest, then glanced toward each other with a shared smile that suggested they felt good about being in the right hands.