After consistently being rejected by potential adoptive families during her childhood at the Blessed Sisters of Merry orphanage, Michelle Darnell (Melissa McCarthy) grows up to become a highly successful, but hardened and cynical, businesswoman. Placing profits above notions of friends and family, Darnell betrays her mentor Ida (Kathy Bates), her lover Renault (Peter Dinklage), and her loyal assistant Claire (Kristen Bell). When the industry titan is arrested for insider trading, her company is usurped by Renault and all of her possessions are sold off, leaving her destitute when she's released from prison four months later. Arriving on Claire's doorstep, Michelle convinces her former employee to let her stay until she's able to bounce back. With Claire and her daughter Rachel's (Ella Anderson) help, Michelle must attempt to reclaim her empire – and overcome her own contentious nature.
Starting off as a celebrity motivational speaker, complete with rap stars, dancers, and pyrotechnics, Michelle is anything but the typical Wall Street hotshot. So it's particularly baffling that the movie would retain the name "The Boss," a moniker never actually applied to McCarthy's character in any manner fittingly representative of the filthy-rich, mobster-type persona depicted on the theatrical poster art. Whatever the title was intended to mean, it gets utterly lost amidst a series of incoherent, spontaneous modifications for the leading role, which shifts around so much it's as if she's depicting multiple personalities. When the story diverges into a Girl Scouts cookie/brownie-selling rivalry and showdown, Michelle's former multimillions CEO status becomes virtually blotted out.
The very first verbal gag, which is a derivation of the "Who's on First" routine first popularized by Abbott and Costello, descends into blathering babble, as if half a joke was written and then dropped. This gives way to a series of conversations that all fall comparably flat - perhaps setting some sort of record for the most number of completely unfunny blabbers spouted out in a row, gruelingly unable to land a genuine punchline. The exchanges are painfully spewed, as if the actors were laboring through their dialogue while fending off boos from a live improv crowd. Even the slapstick, which generally capitalizes on the easy target of McCarthy's weight, struggles to find its footing.
"You've got no capital and nobody likes you!" The plot comes together discordantly, with flashbacks and transitions so ineffective they appear as if pilfered from different films. The basic ideas are hastily and sloppily sewn together from a smattering of varying works - undoubtedly pulling from rejected subplots from other Ben Falcone/Melissa McCarthy scripts. Is Darnell trying to regain her business acumen? Is she trying to display an emotional or maternal side? Is she trying to save her employee-turned-partner from the monotony of life as a single mom in a dead-end job? Is she trying to redeem herself from a career of backstabbing and deceit? Is she trying to find a suitable man for Claire?
As each wholly incompatible predicament arises, the calculations and the resolutions either carry on too long or cut off too soon. The comic timing is disastrously unpolished. And the villain is another strong example of how incautiously the storyline is concocted - he's a bitter ex-lover, a rival businessperson, an extreme eccentric, and a samurai enthusiast all rolled into one, proving to be more of a cartoon character than a believable human being. When deadly conflict (something that should have never appeared in this kind of project) transforms into reconciliation with a couple of quick jokes, it's clear that nothing about "The Boss" was well thought out or approached with common sensibility (especially when the money to buy bags, stickers, ribbons, berets, and all the brownie ingredients is totally ignored). But, more unforgivable than the lack of substance, is the fact that so many of Michelle's misadventures are just plain humorless.