Act One

At a Chicago nightclub in the 1980’s, the band The Loop appears on stage for a concert. The band members include guitarist JJ, drummer Eli bassist Glenn, and Bobby Stivic, the lead singer. Bobby comes on stage and welcomes the audience, and they sing (“Overture/Bobby’s Daydream”). The performance abruptly stops and JJ, Eli, and Glenn exit. The semblance of a rock concert disappears into the office break room of Stone Incorporated, a cardboard packaging company in Milwaukee, Wisconsin, and we see that Bobby was daydreaming while listening on his Walkman to his old band’s demo.

Roz, a sassy, southern HR exec enters to tell him his break is over. She takes his tape and warns him that daydreaming is not a good look if he wants to be promoted to an executive sales role. Bobby returns to the assembly line and starts folding boxes on the conveyor belt. Mr. Stone, the company owner, accompanied by his daughter Cassandra Stone, the accountant, addresses the employees, reassuring them that the company is not in trouble and that tomorrow begins the 1987 Midwest Packaging Convention, which is their biggest sales weekend of the year. Bobby tries to convince Mr. Stone that playing music will increase productivity and boost company morale and hands out a box of Sony Sport Walkman’s to Stone, Roz, and each employee (“Hip to Be Square”). He reveals that he acquired them from Stereo Hut after he made an unauthorized deal by offering them a holiday rate which Cassandra states will cost the company a lot of money. Stone fires Bobby for his mistake; Bobby tells Cassandra he was only trying to help and will find a way to pay off the company’s losses and make things right.

Roz overhears and Bobby tells her he has a plan to fix his mistake, but he needs her help. He explains that working at Stone Inc is more than a job to him; it’s his future. He barely made it through high school and wasted a decade in an unsuccessful band but now he wants to be someone (“Be Someone”). He shows her a conference program with Swedish furniture mogul Otto Fjord featured as the keynote speaker. Fjord is bringing his business to Chicago and Bobby wants to recruit him to be Stone Inc’s newest client. He asks her if he can crash with her in Chicago so he can meet him, she reluctantly agrees.

At the Drake Hotel lobby in Chicago, Cassandra is shocked to see her best friend Paige who, with her husband Wyatt in tow, is taking her first break from her six month old newborn baby. Paige thinks Cassandra overworks herself and invites Cassandra to their Princeton reunion which is also happening that weekend. She tells Cassandra she has a guy for her to go on a blind date with and Cassandra begrudgingly accepts to have one drink with him (“Don’t Make Me Do It”).

Bobby and Roz are in search of Fjord at the hotel. Bobby tries convincing the Head Hotel Porter to give him Fjord’s room number by offering to bring Fjord’s bags up for him and hooking him up with White Sox game tickets for him and his kid. The Porter takes him up to the Dick Butkus Suite.

In the suite, Fjord is being interviewed by Mike Wallace from 60 Minutes about his new furniture store, IDEA. He talks about his traumatic childhood as an orphan and how that led to his success. Bobby brings him his luggage, Fjord thanks him and tips him. Bobby claims he is there on behalf of Stone Incorporated, and they could save him money on furniture shipping costs. Initially Fjord is not interested in his proposal, but Bobby tells him he believes that destiny brought them together; this deal is not just for profit, but for creation (“Do You Believe in Love (Reprise)”). Fjord admires Bobby’s desperation and invites him to a meeting the following day at the hotel spa sauna. 

On the convention hall sales floor, Cassandra wears a cardboard-shaped skirt and is gearing up her own sales pitch to prospective clients at the conference. Stone tells her she’s out of her depth, and lectures Cassandra about the differences between accounting and sales while Roz and executives chime in (“Working for a Livin’”). Cassandra hears their point and asks for a company sales handbook to hone her pitch, but Stone tells her sales is about instincts. Cassandra attempts to use her instincts to acquire new clients, but fails miserably as she is used to having direct directions and order (“I Know What I Like”). 

Bobby sees Cassandra and she is confused about why he’s there. He tells her he is trying to save the company, and she brings up the fact that he was fired. He tells her he discovered that the company has been running at a loss and Stone has been hiding it; going so far as to take out a second mortgage to cover payroll. Cassandra says they will need double the ten million units to cover the losses and become solvent. Bobby explains his plan to get Fjord as a client and asks Cassandra to help him close the deal which unnerves her. Bobby explains he has experience in how to “sell” things from being in a band and he can help her feel less nervous in high pressure social situations (“It’s All Right”).

Across town, in Glenn’s mom’s basement, Bobby’s former bandmates, Glenn, JJ, and Eli are jamming out to “Couple Days Off”. JJ and Eli feel that Glenn is not the right fit for a frontman, as it’s revealed they have struggled to find one since Bobby left the band. Eli tells Glenn he sent Bobby a demo of their song and that he is back in town. Bobby comes back in a business suit, and while JJ and Eli are excited to see him, Glenn is resentful of Bobby abandoning them a year ago. Eli explains that they are performing at The Metroplex, and they hope he can join them, but Bobby declines on account of his conference responsibilities. They remind him of the songs he wrote when they used to perform together (“I Never Walk Alone/Finally Found a Home”). Bobby apologizes for leaving them and they beg him for one last show. Bobby reveals he pawned his dad’s guitar a year ago to buy a bus ticket out of Chicago and that he is done with music. He tells them they shouldn’t do the show at all and should get out of show business and find a career like he did.

In the Lake Michigan Room of the Drake Hotel, Tucker, Wyatt, and three of their college friends sing acappella as The Undertones at their reunion (“That’s Not Me”). Paige wants to pair Cassandra with her ex, Tucker who is back from Tokyo but she is apprehensive about it. Cassandra admits to Paige she focuses on work because her dad needed her after her mother’s death. Tucker and Wyatt approach them and Cassandra grabs Wyatt’s hand to take him to the bar but he takes a phone call from Tokyo, so she goes to the bar on her own. Cassandra and Tucker catch up on the last three years since she moved home to Milwaukee from Chicago, forcing them to break up. He tells her he is still interested in her and wants her to let him in, but she wants to leave it all in the past (“Give Me the Keys”). As she heads back to the hotel, Tucker asks her how Stone is holding up after the death of his wife. Cassandra tells him he is hanging in there. Tucker mentions that at their college graduation, Cassandra’s Mom told him she was really happy that they found each other. This weighs heavy on Cassandra as she tells Tucker goodnight. 

The next day, Bobby and Fjord are in the Sauna in bath robes. Fjord tells him he is ready to order 30 million units for 50 cents per unit. Bobby explains that he is not authorized to make the deal, but Fjord thinks it’s a stalling tactic and pushes Bobby into agreeing to the deal. Stone, Cassandra, and Roz all enter the sauna, and Fjord tells them about the deal. In shock that Bobby made the deal without her present like they planned, Cassandra tells Fjord it is not possible because the price of pulp is doubling next quarter, and the deal will bankrupt them. Fjord tries to leave, but Cassandra stops him and takes over the meeting. She nervously but earnestly gives her pitch, mentioning the company’s family history and how they gave up a lot for the business. She grows confident and gets an agreed upon deal for fifty-six cents a unit on Fjord’s condition that she and Bobby oversee Fjord's sales account (“The Pitch”). 

Afterwards, Bobby and Cassandra are alone in the sauna and Bobby opens up to her about his family and tells her his dad died when he was thirteen in a car accident. He explains that his Dad was barely around because he was chasing a record deal. Cassandra mentions how difficult things have been for her since her Mother passed away. They are both still learning how to live with loss. Bobby asks Cassandra if she has plans later.

Backstage at The Metroplex, Eli, JJ, and Glenn are stressing out about their performance. Glenn is doubting himself and doesn’t feel that he can play and sing at the same time. Bobby walks in and the band are relieved and overjoyed to see him. They go on stage and sing together, reunited as The Loop (“Do You Believe in Love”). Paige, Wyatt, and Tucker arrive in the front row and when Bobby sees Cassandra in the crowd, he sings to her, which angers Tucker. Bobby pulls Cassandra on stage, and they sing together.

After the concert, Cassandra makes her way backstage with Tucker, Wyatt, and Paige. Bobby introduces himself to her friends who congratulate him. It is obvious to everyone that there is a connection between Cassandra and Bobby. As tension mounts between Tucker and Bobby, Wyatt swoops in to pull Tucker away for their reservation at Trader Vic’s. Wyatt, Paige, and Cassandra leave but Tucker stays back to have one last word with Bobby. Tucker makes it clear to him that he and Cassandra are together and Bobby needs to back off. Wyatt comes back and pulls Tucker away before things escalate.

Glenn, JJ, and Eli rush over to tell Bobby news that the band Neon Thunder need new openers for their North American tour and Chrysalis Records offered them gig. The tour lasts for a year and begins at The Palladium in New York in a few days. Bobby is torn; of course he’d love to go on tour but he also just made a commitment to Stone Inc and Fjord. The band reminds him that this has been their dream since they were kids (“The Heart of Rock and Roll”). Bobby pushes through his doubts and agrees to go on tour with them. The band celebrates, but it’s clear Bobby still has mixed feelings about leaving his new life behind.

Act Two

The following morning at the fitness area of the Drake Hotel, Danny Razzle, a high-intensity aerobics teacher, leads a class including Cassandra and Paige (“You Crack Me Up”). Paige asks Cassandra about her relationship with Bobby and pushes Cassandra to give Tucker another chance.

After the workout, Tucker and Wyatt discuss an upcoming call with Milwaukee National Bank, and Tucker says there might be an opportunity there. He then goes to find Cassandra and offers to take Cassandra for frozen-yogurt. Before she can decline, Paige gives her a look and she agrees. Tucker asks if Wyatt would be able to handle the call with the bank alone. Paige tries to get Wyatt’s attention, but he leaves to make the call and promises to make it up to her.

In their hotel room, Bobby and Roz discuss Bobby’s band booking the North American Tour (“It’s All Right (Reprise)”). Roz warns Bobby that if they leave on the tour, Fjord will back out of the deal and Stone Inc will go under. Bobby laments the situation, wishing he could somehow do both.

At Roz’s urging, Bobby signs his new employment contract to be a sales executive at Stone Inc. As she leaves with the contract, Eli, JJ, and Glenn storm into the hotel room, mistakenly assuming that Bobby and Roz spent the night together. As Roz leaves, Eli tells Bobby that Chrysalis Records faxed over the touring contract. Eli tells Bobby he has until 6pm tonight to sign it and get on the bus.

Bobby tries to tell them that he signed the Stone Inc contract, but before he can, Eli, JJ, and Glenn gift him the Stratocaster guitar that he pawned; they pooled every last dollar they had to repurchase it. The friends leave Bobby alone with the guitar. Bobby has a moment with the guitar, and he gives in to playing it (“I Want A New Drug”).

Back on the convention floor, Stone, Cassandra, and the other executives break down their booths. Cassandra and Stone talk about the company and how much Stone has given up, and Cassandra reveals that she knows about the second mortgage and how her father has been covering payroll out of his own personal savings to keep the company afloat.

Stone tells her that he’s been hanging on too tight to the past; he thought he could keep things the same as when his wife, Cassandra’s mom, was here. They begin to reminisce about when they were a complete family, remembering back when Cassandra was a child (“Doing It All For My Baby”).

Fjord, Bobby, and the other executives arrive and Stone announces Bobby as the newest sales executive. Bobby tries to interject, but Stone playfully tells him it’s too late; he’s under contract now. He then announces that he is retiring and Cassandra will be taking over t as CEO..

Paige, Wyatt, and Tucker congratulate Cassandra on her promotion. Tucker tries to convince Cassandra they are a perfect fit together, and offers to move his office to Milwaukee to be with her and start their lives together (“Stuck With You”).

He proposes to her with his grandmother’s ring, but Cassandra, after imagining what their married life would be like, declines the offer. Tucker leaves. Cassandra laments about the awkward situation and then leaves as well. In the wake of this, Paige and Wyatt realize how lucky they are to have found each other and decide to go back to their hotel room together (“Don’t Make Me Do It (Reprise)”).

Cassandra reflects on Tucker’s proposal as Roz comes back after forgetting a briefcase. Cassandra asks if Roz has a special someone, and Rob answers that she does: Herself. Roz then tells Cassandra it’s important to find someone who loves her for who she is, not who she was. 

Bobby sits on the roof of the hotel strumming his guitar (“Power of Love (Reprise)”). Cassandra approaches, tells him that her relationship with Tucker is over, and kisses him. They immediately pull back from the kiss and say they can’t be together because they work together; they aren’t thinking straight. Bobby leaves. Cassandra tries to grapple with what just happened (“It Hit Me Like A Hammer”). 

Bobby enters his hotel room to find Roz holding up both signed contracts. Bobby tries to explain himself but Roz tells him that she understands, and reveals that she was in a band once, too, back in college, but her mom threatened to pull her tuition. But Roz didn’t listen and continued to be in the band until her mom showed up to one of her concerts and convinced her music was a road to nowhere. Roz quit the band soon after that and gave up her dream to live her mom’s dream. She tells Bobby he has to make a choice, just like she did (“Back in Time”). 

As Roz leaves, Bobby gets two phone calls, both with “good news”: One from his band and the other from Cassandra. The band tells him that they now have an agent, they’ve been signed to a record deal and the label wants Bobby to write an album for them to record for the label’s big spring push. Cassandra tells him that Fjord also wants to give Stone Inc his mail order business.

Later that evening at The Metroplex, JJ, Glenn, and Eli wait for Bobby as the roadies pack their equipment onto the tour bus (“Jacob’s Ladder”).

Bobby shows up to tell them there are some loose ends he needs to tie up. He gives them his guitar case to load on to the tour bus. His friends chastise him for making them wait and he tells them he’ll catch the first flight to New York in the morning but promises that he will be there.

On the roof of the Drake Hotel, Cassandra and Fjord discuss the future of IDEA as Bobby comes in and grabs a bottle of champagne. As he pours, Paige, Tucker, and Wyatt storm in and Tucker exposes Bobby’s plan to go on tour with his band for a year. Fjord tells Bobby that he has betrayed his trust and the deal is off.

Cassandra demands to know what’s going on and tells Bobby that she put her faith in him and now she must fix this. Tucker interjects that she need not bother; he called the bank that owns the company debt and bought it, and he will soon own Stone Incorporated. He tells her that if she cooperates, he might let her keep her job. Cassandra leaves and Paige follows after her. Wyatt turns to Tucker and questions his decisions, and Tucker replies that it’s just business and to get Paige in line. Wyatt slinks off leaving Tucker and Bobby alone.

Tucker taunts Bobby by calling him a loser just like his father. Bobby almost punches him but decides against it and Tucker leaves Bobby all alone (“The Only One”). 

Eli finds Bobby and hands him a letter they found wedged in the guitar case after a roadie dropped it. It’s from Bobby’s dad and was written the night he died. JJ and Glenn tell Bobby there is more to his dad’s story than any of them ever knew: He finally got his record deal, but he turned it down and gave it up to come home to his son (“Perfect World”). 

The band tells Bobby that whatever he decides, they will support him. Bobby tells them he loves them and will never let them down; New York is not gonna know what’s hit it. (“Be Someone (Reprise)”).

That night at the Midwest Packaging Convention Awards Ceremony (“The Awards Ceremony”), Stone gives his Lifetime Achievement Award speech and reflects on his life and the difficult choices he’s had to make. As he finishes, Bobby bursts into the ballroom holding a boombox to declare his love for Cassandra (“If This Is It”).

Tucker tries to interject, and Cassandra tells him to leave because his hostile takeover failed. Cassandra convinced Fjord to come back in on the deal. When Cassandra asks Bobby how she can ever trust him again, he tells her he’s not going on his tour (“Giving It All Up For Love”). 

Bobby tells everyone that the band is going to open in New York with the song he wrote, the first of many, and that The Loop has a new lead singer: Roz (“The Power of Love”). Bobby and Cassandra kiss while the convention rejoices.