Lord Mercer announces that he is making his 19-year-old daughter, Milan, the new store president.  She is disgusted, but he hopes that the job will teach her some responsibility.  Lord Mercer tells Drew that he must make sure Milan does a good job or lose his co-manager position.  She messes up a negotiation with a union by bringing in her boyfriend, D'Artagnan, and groping him the whole time.  Drew asks Kate to talk to Milan and convince her to focus on her job instead of devoting all her time to her boyfriend.  Milan takes her advice and gets dumped.  She forces Drew to go work at the docks.  Kate feels bad for Drew and agrees to try to get D'Artagnan to take Milan back.  Kate instead sleeps with D'Artagnan just because he gives her some stupid look.  Milan plans to give Drew his old job back, until she learns what Kate has done.  Milan vanishes on the day that her father has come in to check on her progress.  Drew sees her on the edge of the building preparing to jump.

Bringing Up Boss (1)

Drew Carey

Ryan Stiles

Diedrich Bader

Christa Miller

Craig Ferguson

Kathy Kinney

John Carroll Lynch

Sam Simon

Daddy Dearest (2)

It's a Dog Eat Drew World

Teenage Drew visits a doctor and learns about his 'changing body'. Lewis and Oswald show SheDaisy their talents as backup singers. Kate and Jenny make out during a sleepover and are upset at the guys gawking at them. This episode was recorded in the style of a sketch show. Drew hosts a film about the dangers of cooties. Mimi bothers Uncle Kracker for help with a crossword puzzle. Oswald the cop goes undercover in a high school in a terrible disguise.

Drew Carey's Back-to-School Rock 'n' Roll Comedy Hour (1)

Drew hosts a film about the dangers of cooties.  Another film shows girls how cheerleading can help them later in life.  Mimi bothers Uncle Kracker for help with a crossword puzzle.  A clueless police officer goes undercover while still wearing his uniform.  Peter Frampton recalls his past romance with Mimi.  A talking zit gives a young man questionable dating advice.  Mimi tries to convince Sugar Ray to stay over at her place after the show.  Drew compliments teachers, with the exception of his elementary school teacher, Ms. Freeman.  He boasts that math isn't necessary in life, only to miss out on a party because Mark McGrath of Sugar Ray tells him the location in the form of a story problem.

Drew Carey's Back-to-School Rock 'n' Roll Comedy Hour (2)

Drew is finally released from the mental institution.  On the day of his release, he runs into Nicki at the Warsaw.  She reveals that she is divorced, and feels she made a mistake in letting Drew go.  Kate worries that Nicki is going to hurt Drew again.  Kate, Lewis and Oswald try to create a distraction to help Drew get away, but he assures them that he is all right.  After his friends leave, Drew suddenly proposes to Nicki.  She accepts, and they marry in Pennsylvania.  Drew's friends cannot find him for several days.  Kate admits to Lewis and Oswald that it made her very jealous to see Drew with Nicki.  She realizes that she still loves him.  She calls Drew on his cell phone and arranges to meet him at a bar near City Hall.  Drew returns home with Nicki and announces their marriage.  He leaves to meet Kate before Lewis and Oswald can warn him of her intentions.  She proposes to Drew, who immediately accepts.  Meanwhile, Steve refuses to forgive Mimi for driving his brother insane.

Drew Gets Out of the Nuthouse

Lewis and Oswald decide to buy a house after being convinced that they can't find a date because they live on top of a bar. Meanwhile Drew tells them he is married to both Kate and Nicki and asks them to keep the fact concealed to both women till he can tell them the truth himself.

Married to a Mob

Drew manages to convince Kate that Nicki made the wedding cake herself because she is crazy.  He becomes desperate to clear things up as soon as possible.  With Steve's help, Drew realizes that Kate is the woman he really loves.  He decides that he will explain everything to her and beg for forgiveness.  Before he gets a chance, Kate and Nicki figure it out on their own.  They turn to Mimi to help them get revenge.  She is reluctant because she wants to prove to Steve that she has changed, but gives them some advice.  Drew meets Kate at the Warsaw to confess.  She claims that she blames everything on Nicki, and races off to Drew's house in a rage.  They stage a fight and throw a mannequin out the window onto his car.  They both confront him, and an already furious Nicki leaves after learning that Drew has jilted her.  He pleads with Kate for another chance, but she says that she never wants to see him again and peels out in her car.

When Wives Collide

Nicki talks to the newspaper about Drew's bigamy.  The article also refers to his marriage to Mr. Wick, and everyone around town starts calling him "the impotent, bisexual bigamist." Drew's lawyer tells him that his marriages to Kate and Nicki are invalid because he is still married to Wick.  Kate refuses to speak to Drew, and begins dating a handsome local sportscaster.  Drew tries to come up with a grand gesture in the hopes of winning her back.  Inspired by a marriage proposal on the side of a bus, he buys an ad asking for forgiveness and has it placed on five buses.  He buys just half-ads to save money.  Unfortunately, his messages share space with an anti-child abuse campaign, and the pictures are arranged in a way that makes it seem that Kate is the woman who battered the child in the photo.  Kate's boyfriend dumps her to preserve his image.  Instead of helping Drew with a new plan, Lewis and Oswald pay a woman to become a substitute Kate.

Bus-ted

Drew decides to fill some of his free time by taking a ventriloquism class.  Winfred-Louder gets a new owner, the easy-going Mr. Newsome.  He identifies with Drew because he spent many years in middle management before he got rich.  Drew organizes the store's charity Halloween party.  Kate shows up as herself, in a wedding dress with a fake knife in her back.  Mr. Newsome tells Drew that he wants him to replace Wick as store manager.  He plans to make the announcement to the board the next day.  Seconds later, Newsome gets spooked by a fake bat and drops dead of a heart attack.  After Lewis has DrugCo preserve the body, Drew brings it to the board meeting the next day and does his ventriloquism act.  He gets Mimi demoted, but becomes too cocky and tries to drink a glass of water while talking.  He drops Newsome before he can appoint himself manager.  Lewis winds up looking like Frankenstein's monster after a visit to a deranged dentist who works on a boat.

It's Halloween, Dummy

Drew's parents come to visit, but decide to stay with Steve and Mimi so that they can spend more time with the baby.  Beulah confesses to Mimi that George has never satisfied her in bed.  Mimi tells her to talk to George about this problem.  He becomes furious and shows up at Drew's house with his bags to announce that he is leaving Beulah.  After Mimi persuades a horrified Drew to give George some advice, he and Steve have a very awkward talk with their father.  Lewis and Oswald build a killer robot in the hopes of winning $1000 in the Warsaw's Battle of the Bots.

Beulah Gets Her Groove Back

Drew awakens to find himself handcuffed to former Cheers star John Ratzenberger in a Tennessee dog pound.  John says that he saved Drew from jumping off a bridge in a drunken stupor as he ranted about some terrible thing that he had done.  Drew tries to re-trace his steps and figure out what happened.  He headed to Nashville for a convention, and Oswald and Lewis tagged along to visit Dollywood.  Mimi and Steve used the absent Wick's ticket to take the trip, and decided to have sex on the train.  Drew became ill after drinking a beer and stumbled into the wrong cabin.  He remembers that Mimi entered the cabin as the train went through the tunnel.  Drew finds blue paint all over himself and fears that he had sex with Mimi.  Oswald and Lewis tell him that Mimi discovered that it was Drew and left him alone.  The Blue Man Group then covered him in paint as part of one of their experiments.  Drew discovers that John Ratzenberger drugged his beer and led him to the wrong cabin.  He and the

Drew Live III

Winfred-Louder hires an efficiency expert, Christine, to look after the store while Mr. Wick is away.  She is a very demanding taskmaster, but goes easy on Drew because she has a crush on him.  Mimi and Nora try to convince him to date Christine so that she will ease up on the employees.  Mimi gives him a check for $500 in exchange for sleeping with Christine.  He refuses, but she leaves him the check and asks him to think about it.  Drew agrees to a date with Christine.  She explains that she is tough on the staff because she wants to increase productivity so that she won't have to lay off as many people.  Drew and Christine discover that they have a lot in common, and end up sleeping together.  She finds the check and believes that Drew only slept with her for the money.  He tries to explain, but she threatens to fire him if he brings up the subject.  He finally goes to her apartment on Thanksgiving, and leaves a message when she won't see him.  He repeatedly talks about the fact tha

Eat, Drink, Drew, Woman

Drew begins to feel emasculated when Christine repeatedly bosses him around and has him do all of her errands.  Mimi prepares to buy a minivan.  She is heartbroken when Dee Snider of Twisted Sister shows up at the office and tells her that she can no longer be president of the group's fan club, as she has been neglecting her duties because of motherhood.  She grows dissatisfied with her life and longs for the excitement of her past.  She decides to buy a convertible sports car instead of the minivan.  She runs into Drew, who is driving Christine's sports car, and they decide to have a race.  They are both thrilled by the experience, and begin sneaking out and taking part in drag races every night.  Steve finds out and shows up with Gus to convince Mimi to stop racing.  Christine learns why Drew has been racing, and agrees to be less demanding.  After the racegoers make fun of him for being a wuss, she lets him race one last time.

Mr. Laffoon's Wild Ride

Mr. Wick, in a teleconference from Hawaii, announces that all employees below store manager must have a 20 percent pay cut.  To make up the lost income, Drew rents out his spare room to a gay couple.  Lewis and Oswald consult the men for help decorating their new house.  Mitch and Les use their connections to help Drew get a job interview at a better store.  Drew gets the job, but fears that he is in way over his head.  Mitch and Les encourage him to have faith in himself.  Drew is told to cut $200,000 from the store's budget by the end of the week.  He finds a way to effectively streamline personnel and eliminate unnecessary positions.  Unfortunately, he winds up proving that his position isn't essential, and gets fired.  Mitch and Les announce that they are moving out, as they have inherited a house.  Wick shows up and admits that Winfred-Louder has fallen apart without Drew.  He begs Drew to come back, but he refuses.  He insists that something better will come along.

Hotel Drew

Drew takes a job as a security guard.  Lewis, Oswald and Steve tell him that Kate has gotten a promotion.  Drew is upset to realize that she no longer comes to him with news about big events in her life.  He asks his boss to transfer him to the Rock and Roll Hall of Fame so that he can spend more time with Kate.  Christine isn't too thrilled about this, and doesn't believe Drew's claims that he just wants Kate as a friend.  Kate becomes annoyed when Drew tries to hang around her at work.  While searching for his keys at the Elvis exhibit, he finds a previously unheard record in the couch.  It features Elvis singing Jewish folk songs.  Drew gives Kate credit for the discovery, which will give her a huge career boost.  Mimi predicts that Kate will blow it.  While showing off all of the precautions she has taken with the record, Kate ends up dropping a steel case on it and damaging it beyond repair.  She decides to accept a job offer at a polka museum in Chicago before word gets out about

Drew and the King

Oswald and Lewis make a video about themselves to impress women, but it doesn't have any effect whatsoever. The gang gets the wrong end of the stick when Drew tells of his encounter with Mr. Wick's mother, and Oswald reveals some disturbing feelings.

The Curse of the Mummy

On Drew's first day as co-manager, he and Wick learn that the store is going out of business.  However, a potential new buyer has stepped forward and may agree to save Winfred-Louder.  The group's main representative, Lord Mercer, doesn't like Drew; but gets along well with Wick, as they are graduates of the same college.  Wick promises to handle the deal himself.  Drew does not realize that Wick has resumed drinking until he falls down the stairs at the Warsaw.  The buyers are bored with Drew's presentation, and insist on hearing from Wick.  He refuses to help unless Drew lets him drink.  He charms the buyers and helps win them over.  A guilt-ridden Drew wants to take Wick to rehab, but decides that he must let him keep drinking until the deal has been finalized at a cocktail party the next day.  Wick gets totally wasted and ends up punching out one of the investors.  The deal is called off, until an apologetic Drew confesses to letting the alcoholic Wick drink.  Lord Mercer is impres

The Enabler

Lewis and Oswald enter a baby into Winfred-Louder's beautiful baby pageant to raise money to replace the heating ducts they broke. To get an edge over the other contestants, they try to teach the baby a talent which impresses the judges until they push it too far.

Pretty Baby

Drew, inspired by his short stint as a security guard, buys a police scanner.  After hearing of an incident at the Warsaw, he races over to the bar and tries to offer his assistance to the police.  An attractive cop decides to go out with him, explaining that she wants to take a break from dating good-looking guys.  Drew soon discovers that he and Marlo have nothing in common, and his health goes into decline because of her constant smoking and his allergy to her cat.  He plans to break up with her, but becomes terrified of the consequences after seeing her rough up a guy whose only offense was a broken taillight.  Oswald and Colleen ask Lewis to give them some time alone at the house.  He claims to have begun dating a co-worker, but actually sleeps in Drew's basement.  Drew finally breaks up with Marlo, who becomes enraged and vows revenge.  When Lewis comes up for a snack late that night, Drew believes that Marlo has come after him.  He shoots Lewis in the leg.  Marlo concludes that

A Shot in the Dark

Drew is upset when Lewis, Oswald and Kate begin neglecting him to devote more time to their jobs.  Steve also cannot spend time with him because of plans with Mimi.  A vicious stray dog shows up in the yard and tries to steal a sandwich from Drew and Speedy.  A depressed Drew has lunch with Mr. Wick after his friends stand him up.  They find that they have common interests, but Wick quickly scares him off by making plans to spend every minute of the day together.  Drew tricks Lewis, Oswald, Kate and Steve into coming over by claiming an emergency.  They are upset to learn that he just wants to play a game of Risk, and try to leave.  The wild dog returns as part of a pack.  The dogs surround the house, even cutting off the phone lines.  They fake an attack on a small dog, who lets them into the house after the gang brings him inside to help him.  Everyone must flee to the basement, where they pass the time by reading Drew's old journal and singing songs.  Mimi comes by in the morning lo

Lord Mercer refuses to show concern for Milan, claiming that she regularly threatens to kill herself to get attention.  Drew gets her to come off the ledge.  Drew is upset when his father refuses to congratulate him for his promotion, instead sending him a fish wrapped in the newsletter that announced his new position.  Lord Mercer fires Milan for repeatedly refusing to show up for meetings.  She feels that she has no reason to make an effort because her father is never satisfied by anything she does.  Drew, inspired by his own situation, pleads with Lord Mercer to give Milan another chance.  He promises to help her do a better job running the store.  However, Milan only knows how to do one thing--party.  She throws a rave in the store.  It seems to be a disaster, but actually boosts sales considerably.  Lord Mercer still disapproves because raves are bad for the store's reputation.  Milan decides that she doesn't always need to seek her father's approval.  Meanwhile, Lewis inadvertent

Drew spends his entire vacation home sick with the flu.  Milan prepares for her 19th birthday party, which will take place in Spain and feature many supermodels.  Lewis and Oswald decide to apply for second jobs as airport security guards so that Oswald can afford his nursing school tuition.  After Drew whines about never getting to travel anywhere, Milan invites him to her party.  Oswald and Lewis get the jobs, and are extremely overzealous and incompetent (big surprise).  Drew tries to cut in line and race through without undergoing a security check.  He gets hauled off to a holding cell and misses his flight.  The supervisor refuses to let him board another flight because he has been arrested so many times.  Drew has Kate distract the supervisor by pretending to have lost a baby.  He tricks Oswald and Lewis and runs past them to board the last flight to Spain.  The plan has mechanical problems and lands in Greenland.  He thinks his luck has changed when he meets a beautiful woman, b

Never Been to Spain

Drew is perplexed when Steve attacks one of the other fathers at Gus's kiddie gym with little provocation.  Drew theorizes that Steve is just frustrated at being cooped up with the baby all the time and having no adult conversation.  He hires him to fill an opening in the cosmetics department, despite Wick's objections.  Drew visits Steve on the job and points out some matters that he needs to handle.  Steve suddenly begins pounding a customer who tries to return a bottle of perfume without a receipt.  Kate figures out that Steve's behavior is the result of jealousy over Drew's professional success.  Drew looks at some old home movies and gets Steve to admit that he has always resented him because he liked having their parents to himself.  Steve takes a job as a prison guard to deal with his hostility.  Lewis and Oswald help DrugCo administer an experimental drug that causes empathy in prison inmates.  Lewis takes the drug himself after Oswald points out his lack of sensitivity.  Howev

O Brother, Who Art Thou?

Milan fixes up Drew with her mother, Lindsay, because she wants her to finally meet someone who isn't just after her money.  Drew makes the mistake of allowing Lindsay to drive his car, and they are trapped for several hours after she crashes into a ditch.  Lindsay finds Drew's lifestyle charming, and wants to continue seeing him.  She is scheduled to leave town a few days later, but suddenly announces that she is moving to Cleveland.  Drew is alarmed to learn that Lindsay would lose her $500,000 per month alimony if she ever re-married.  He predicts that she will soon grow tired of the novelty of living like a poor person.  He challenges her to spend one week in his world.  She tries her best to adjust to a simple lifestyle, but really doesn't take to it.  She begins breaking out in rashes and losing her hair.  Drew decides that he is in love with Lindsay for some reason.  After he tells her this, she announces that she is leaving.  She never really liked him that much, and cannot sur

Rich Woman, Poor Man

Lewis struggles to find a date to his ex-girlfriend's wedding.  All of his friends (and even Mimi) try to help him out, but he inevitably drives all the women away with his creepy comments.  Lewis becomes extremely depressed and refuses to get off of Drew's couch.  Oswald brings in Lewis's mother, who reveals to Drew that Lewis has an IQ in the genius range.  His family always kept the truth from him in the hopes that he could live a normal life.  Lewis is thrilled by the news.  He attends a Mensa meeting, but still strikes out with every woman.  He begins to fear that he will never fit in, until a woman shows up at the meeting to deal with the building's rat problem.  She has a high IQ and shares Lewis's love of bizarre trivia about serial killers, etc.  They immediately establish a connection and set off to catch the rat together.

What Women Don't Want

The guys' mothers come to town for a special Mother's Day brunch at the Warsaw.  Kate introduces everyone to her new stepmother, who looks exactly like her.  Beulah praises Steve for getting married and starting a family of his own, and all of the mothers nag their kids to follow his example.  A web site publishes a list of the biggest Internet porn users in Cleveland, which is scrolled onscreen during the news.  The moms are mortified to discover that Drew, Kate, Lewis, Oswald and Wick are on the list.  The gang sues to have its names taken off the list.  The mothers, led by Beulah and Mrs. Wick, decide to move back in with their kids to get their lives back on the right path.  They throw out all of their porn and beer and generally drive them crazy.  Mimi's grandmother feels that the women should lighten up.  After Beulah catches Drew drinking, she and the other mothers elect to testify on behalf of the anti-porn users site.  Drew represents the gang after its lawyer proves incompete

Look Mom, One Hand!

A woman named Kathy applies for a job at Winfred-Louder and takes a liking to Drew.  She isn't right for the job, but makes a date with Drew.  A bald eagle breaks into Drew's house and trashes the place.  No one can attempt to remove the eagle because it is a protected species.  Lewis and Oswald decide to start a cookie business.  The cookies attract two children, one of whom threatens to expose the fact that they have an illegal house in the park.  The guys must give him cookies and do his homework.  The eagle moves to Drew's roof.  Kate changes her attitude about protecting the eagle after it craps all over her dress.  Kathy brings her dog along on the date, but leaves him outside.  The eagle snatches it and flies away.  Lewis and Oswald find the dog at the pound after the eagle drops it.  When Drew tries to tell Kathy what happened, the eagle steals her dog again.  She blames Drew and runs off in disgust.  Lewis and Oswald try to lure the eagle away with pheromones, but they get spi

The Eagle Has Landed

Lord Mercer and Milan celebrate their financial success by giving the employees fancy new desks.  They later learn that their accountant has cleaned them out, and have to lay off a bunch of employees.  Drew, Mimi and Mr. Wick are forced into duty on the sales floor, where Drew sells underwear.  When the store continues to flounder, Lord Mercer converts it into a discount outlet.  Nicki sends Drew a gift and claims to have forgiven him.  Drew is suspicious, but decides to meet with her.  She has gained back all of her weight and is homeless.  She tries to shoot Drew, but drops her gun.  Drew feels responsible for her problems and offers to let her stay with him.  Nicki finds a knife in the kitchen and thinks about stabbing him, but is distracted by cheese and decides that she can kill Drew later.

The Underpants Guy

Drew is an assistant director of personnel in a Cleveland department store and he has been stuck there for ten years. Other than fighting with co-worker Mimi, his hobbies include drinking beer and not being able to get dates. To make a few extra bucks he has a micro-brewery going in his garage with his buddies.

Bringing Up Boss (1)

Seasons9

Season 7 Episodes27

Cast7

Crew1

Discussion

Episode Summary