Cybill's efforts to end Jeff's overextended stay above her garage stall out when her ex gets fired from his job as her stunt double when he confesses he is afraid to do the required scene. A desperate Cybill tracks down Jeff 's mentor, Stitch Sullivan, in hopes that he will be able to help Jeff overcome his fears. Stitch reminds Jeff of the one and only reason any guy becomes a stunt man: ""world class Hollywood nookie."" Almost instantly Jeff is back on the job. However, Jeff has another case of the jitters on his next job, a film directed by Peter Bogdanovich. Cybill tries to lend Jeff some moral support. When that doesn't work, she starts telling him everything she hated about him when they were married. Within seconds, Jeff jumps off the balcony, completing the stunt in perfect form. The director is thrilled; that is, until he learns that none of the cameramen got it on film because Maryann had the whole crew engrossed in the proceedings of ""the trial of the century"" on the monitor.
Cybill feels neglected when Maryann becomes preoccupied with her new boyfriend Bob, a bassoonist with the Philharmonic. Lost without her best friend, Cybill tries spending more quality time with her family (who are not interested), then hooks up with old friend Patty, who unfortunately brings her two small children along to lunch. When Maryann spots Cybill with Patty, the jealousy is on the other foot....
Cybill decides to fire her agent Arthur, who drops dead behind Cybill and Maryann while they are toasting "new beginnings". Cybill offers her sympathies to Evelyn, Arthur's widow, and ends up arranging the entire funeral. She learns that Arthur was not the big-time Hollywood agent he claimed to be - most of the people in Arthur's Rolodex have never heard of him. A desperate Cybill arranges for celebrity look-alikes to attend Arthur's funeral. Meanwhile, Maryann confesses to Cybill that she has fantasized about Ira.
To land a movie role as a cop, Cybill prepares by riding with a cop on duty; but when his wife goes into labour, Cybill is left with the car, the siren and a call from Maryann in trouble. Meanwhile, Rachel's husband throws a party to suck up to his academic superior in hopes of landing tenure; and Zoey and Sean notice the academic's wife stealing the silver.
Cybill's hot flashes and herbal treatments don't make her feel any younger, nor does Ira's visiting mother Ruth, who has traded in pantsuits for trendy clothes and "a little sweet wheat". But Ruth is a hit with Zoey, since she arrives in a pink Cadillac that's a present for her granddaughter, much to Cybill and Ira's dismay.
Cybill is disconcerted but delighted when a heartbroken Zoey decides she wants to be best friends; but Rachel storms off when Cybill and Kevin agree to sit in on a marriage counselling session, only to discover that Kevin slept with Rachel's therapist. Meanwhile, Maryann tries to make Ira jealous by flirting with Cybill's Arkansas cousin Lyle, who is obsessed with getting onto The Price is Right.
On the barnyard set of her new show (a parody of Babe), Cybill rescues a pig that was fired and doomed to the frying pan; then tries to keep an independent Zoey from flying the coop after she visits the greener pastures of Paris. Meanwhile, Maryann dresses as Little Bo Peep to entice a sheepish Ira.
When Cybill gets a chance to play Abe Lincoln's wife in the play "What Now, Mrs. Lincoln?" an unexpected caller interrupts her big moment. Meantime, Maryann and Ira gang up on a woman in the audience for her rude behavior - oblivious to the fact that she's the powerful agent Cybill has been courting for months.
After Cybill's house is burgled, she decides to fight back by taking a course in self-defense, installing an obnoxious house alarm, and acquiring a handgun. Meanwhile, the newly-available Ira finds that he has misrepresented himself when he meets a woman at one of Jeff's favorite hangouts - an Alcoholics Anonymous meeting. Maryann becomes a suspect in the abrupt disappearance of Dr. Dick.
After discovering Cybill's picture on an X-rated video, Cybill and Maryann decide to produce an erotic video intended for women. But when Cybill borrows Zoey's laptop to write the script and tries to e-mail it to a producer, she accidentally sends Zoey's European diary instead - and the producer loves the story of how Zoey lost her virginity.
Cybill retaliates when her obnoxious co-star Jack mysteriously fires his friend, the executive producer, Buddy, and apologizes to Cybill for his rude - and crude - behavior. Smelling a rat, Cybill, Maryann and Cybill's producer friend Amy devise a sting operation to trick Buddy into revealing the truth behind Jack's sudden change of heart. Meanwhile, Zoey is having second thoughts about being maid of honor at the wedding of her father, Ira, and Holly after overhearing Holly remark to a friend that Zoey threw her a tacky wedding shower.
Maryann goes home to Buffalo N.Y. for an uneasy reunion with her parents, and to attend a 25-year reunion of her high-school classmates - who treated her like dirt. Maryann learns that her son - who she believed was traveling with Greenpeace - is actually living with her parents. When Maryann consequently opts to forgo the reunion to spend time with him, Cybill goes to the reunion as Maryann in order to claim sweet revenge on the classmates. Meantime, Cybill is also spearheading efforts to make Thanksgiving dinner plans. Zoey gets to try on her hideous bridesmaid's dress, and. as revenge, tricks Rachel into having to wear the outfit as well.
Cybill's overbearing mother Virginia comes for a Christmas visit. Tensions arise when "Me-Maw" showers Rachel with affection while virtually ignoring Zoey. When Cybill confronts her about the favoritism, she learns that Virginia feels a responsibility to compensate for Cybill's own partiality towards Zoey. Meanwhile, Maryann volunteers to be Cybill's personal holiday shopper while Cybill deals with the fact that her show's time slot has been moved - opposite 60 Minutes. Ira finds out that Zoey lost her virginity while in Europe.
Cybill tries to help Maryann, Rachel and Zoey overcome their romantic troubles by forcing them to take part in a new age drum beating session. Maryann, furious when Dr. Dick doesn't send any hateful gifts to her in honor of what would have been their 23rd anniversary, agrees to let Cybill take her to a new age female bonding session so she can get Dr. Dick out of her system once and for all. Meanwhile, Kevin uses Baby William to diffuse his anger towards Rachel and his job-hunting problems, and Ira finds out that Sean cheated on Zoey.
As designated "best man" at Ira's wedding, Cybill is in charge of planning the bachelor party. Since Holly objects to hiring a stripper, Cybill decides to have everyone go to the track instead. But when Ira and the director of Cybill's television series show up expecting to see some skin, Cybill reluctantly agrees to have the party at a strip club. She and Maryann go disguised as men, primarily because Cybill doesn't want to jeopardize her newfound celebrity status. Meanwhile, Zoey tries to get used to her new job as production assistant on Cybill's television show, Lifeforms.
Provoked by Cybill's offensive reaction to a lamb attack on live television, animal activists - led by Shari Lewis and Lamb Chop (as themselves) - launch a campaign against Cybill. Trying to save her career, Andy convinces her to be a guest speaker at an animal rights banquet. Meanwhile, Cybill dates a younger man who seems too good to be true, while Maryann desperately tries to cope with the fact that her new romantic interest shares something in common with her ex-husband - the same name.
Maryann is acting more bizarre than usual during a Valentine's Day outing with Richard and her visiting son. Meanwhile, Zoey moves in with Ira to spite her mother. Sparks fly between Zoey and Maryann's son, Justin. Maryann arranges a Valentine's Day dinner with her son and her new flame but panics and shows up on Cybill's doorstep with Justin and her beau, looking for moral support - just as Zoey is leaving to meet Ira. When Zoey and Justin see each other again - after years apart - they begin spending time together, and, although Maryann loves Zoey like a daughter, she fears that Zoey may break her son's heart. Meanwhile, Cybill spends Valentine's Day with the special guy in her life - her grandson, William.
Cybill and Jeff co-star in a new action film. Just as Cybill is complaining to her photographer friend, DaVolio that her career is going nowhere, Jeff pulls some strings to get her the co-starring role in his new action film. Cybill must then return the favor when she learns that Jeff's future as the next action hero is on the line because he's unable to keep a straight face during intimate scenes. Now that Jeff's making more money than he knows what to do with, he gives Rachel and Kevin a down-payment for a new house.
When Cybill decides to base her character in Ira's new play on Maryann, she begins to shadow Maryann's every move. But, when Maryann tells Cybill that she's not welcome to accompany her one afternoon, Cybill secretly follows her anyway. When she spies Maryann suspiciously meeting a man at his apartment, Cybill assumes that her friend is having an affair, only to discover an even stranger truth.
Cybill joins Ira at an open-mike night for his debut as a stand-up comic, which gets off to a rocky start when he faints from stage fright. Cybill's performance, however, results in an offer to sing in a new Name That Tune. Meanwhile, Maryann displays unusual behavior, but if she seems preoccupied (to the point of wearing the same outfit two days running), it's because she thinks she may be pregnant.
Cybill puts her foot down when she's chosen as a model for a shoe campaign, only to see a billboard with her face on a thinner woman's body. Cybill decides to defend women of all shapes and sizes by defacing the billboard. Meanwhile, Maryann freaks when she discovers that her son, Justin, is two-timing Zoey, and Ira decides to give up caffeine, which creates some abnormal side effects.
When Cybill discovers that Dr. Dick's wife, Andrea (Morgan Fairchild) can get Zoey a piano audition that's otherwise unobtainable, she grudgingly agrees to give a speech at an awards banquet honoring Andrea. But when Cybill finds out that Zoey got the audition on her own, she decides to tell the awards committee what she really thinks of Andrea.
With Cybill as the organizer, Maryann's bachelorette party turns out to be one last evening stalking Dr. Dick. Realizing their stalking days are almost behind them, one last act of torment is in order. Zoey and Rachel join the duo, in a van equipped with the latest surveillance technology, staking out Dr. Dick's house. But mid-execution, Cybill and Maryann overhear "Mrs. Dr. Dick" Andrea tell Dr. Dick that she's leaving him, causing Maryann to rethink her own marriage plans.
The series begins its fourth season with a trip back in time to the 16th century, as Cybill undergoes past-life regression treatment on the advice of her therapist when she begins having erotic dreams about Maryann's jilted beau Richard. She discovers that Maryann's poor choice in men goes back to the days of Henry VIII, when Maryann was Anne Boleyn, and returns to the present just in time to head off a close encounter between Maryann and the despised Dr. Dick. Joining Cybill in the Court of King Henry VIII are Zoey as Ariel's father, Ira as her brother the poet, and Justin as a serving wench.
Maryann is shocked when Cybill tells her she had an affair with a married man - and now wants to rekindle the romance. Maryann reels from Cybill's hypocrisy, since Cybill is always advising her not to even consider going back to the cheating Dr. Dick. But Cybill, head-over-heels in lust with Roger, refuses to admit to her own double standards. Meanwhile, Ira is hurt when he overhears Cybill wonder about what might have been if she had never become Mrs. Woodbine
Zoey rejects Cybill's advice about what to wear for her first piano competition, and Cybill mourns the loss of a mother-daughter moment. After having been brushed off by Zoey, Cybill meets a young girl who welcomes her mothering - and her father isn't bad either. But when he turns out to be a cad, Cybill and Maryann scheme to get revenge. In the meantime, Ira and Justin battle over whose good luck charm Zoey should wear for her competition.
Cybill throws herself into her role when she is cast to play the mother of a sweet teenage girl on a network sitcom. In reality, the girl turns out to be a tough-talking, ultra-hip teen, but Cybill is determined to mentor the difficult youth. The pending birth of Rachel's baby has everyone wondering who will be the godmother, and Maryann is hurt when no one even considers her as a possible choice.
Cybill endures her new role as a sitcom mom, even though she thinks it could mean the end of her career, until her life is shaken up when a 4.0 earthquake rattles the city and inspires her to quit and "follow her bliss". Next thing she knows, Maryann convinces her that they should go to a "schmoozing" where Cybill meets a prominent female playwright. Meanwhile, Rachel shares some shocking news of her own with the family.
Cybill gets a job as a spokeswoman on a cruise ship, but when she and Maryann take a cruise, it turns out to be one of displeasure: Dr. Dick, relentless in his efforts to win back Maryann, puts Cybill in a difficult situation by giving her a letter for his ex that Cybill knows will make Maryann "melt down".
When obsessed fan Minnie steals Cybill's wax head from Madame Tussaud's, the museum simply replaces it with the head of another blonde actress. Cybill and Maryann are outraged, so they concoct a scheme to travel to London and return the real "Cybill-head". Meanwhile, Zoey decides to give up her career as a pianist for an office job, while Cybill and Ira try to save her from a life of corporate drudgery.
When Rachel goes into labor and Maryann has an appendicitis attack on the same day, Cybill finds herself stretched thin trying to care for each of them. After convincing a panicked Rachel that having a second child is a piece of cake, Cybill must reassure Maryann, who is delusional from pain-killing drugs, that her hallucinated dinner party is a smashing success.
It's the year 2027, and Cybill and Maryann, now senior citizens, are still sipping martinis and insulting men. When they come across Cybill's diary from 97, Cybill begins to read aloud from the book, and one of the passages hurts Maryann's feelings - creating a rift between the two friends. Cybill and Maryann must travel 30 years into the past to resolve the issue and discover that their friendship has withstood the test of time for good reason.
When Cybill's garage roof collapses and requires expensive repairs, she tries to get a loan from the bank, only to discover that the loan officer turns out to be her disgruntled former fan, Minnie Arbogast. Adding to Cybill's troubles, Ira accuses Maryann of causing the breakup of his marriage to Cybill. After trying unsuccessfully to reconcile her two friends and resolve her own financial crisis, Cybill gets help from an unlikely source - her former enemy and new-found friend, Minnie.
Following her mother's untimely passing, Cybill finds what appears to be a love letter to an unknown man in Bakersfield. She is shocked that her supposedly conservative mother may have had a longstanding, passionate secret love affair. Curious about this hidden part of her mother's past, Cybill travels to Bakersfield with Maryann and Zoey to deliver the letter to the mystery man herself.
In a fit of romantic nostalgia, Cybill writes a letter to her first love, Bobby Ray, and is pleasantly surprised when he flies in from Memphis to take her out on a date. After spending a wonderfully romantic evening with Bobby Ray, Cybill's faith in love is restored - until she realizes that his criminal history extends beyond being just a thief of hearts. Meanwhile, when Zoey's first love, Gianni, visits from Italy, she worries that seeing him will destroy the magic of their short-lived but passionate romance.
Cybill and Maryann masquerade as ladies of the night to foil an evil prank by the dastardly Dr. Dick. The scheme conceived by Dr. Dick goes wrong when his hired thugs mistakenly drug Cybill instead of Maryann and deposit her in a seedy bus station in the middle of nowhere. To make matters worse, when Maryann comes to rescue Cybill, her car gets stolen and both women end up stranded. The two friends finally get a ride home when two unsuspecting high school boys looking for a good time mistake them for ladies of the night. Meanwhile, Ira tries to instill in Zoey a love for basketball when he gets her a job playing the organ at a Lakers' game.
Maryann's son Justin decides to move to San Francisco for a new job, and Cybill convinces a reluctant Maryann to see a therapist and confront her irrational fear of losing her son. Cybill's suggestion backfires when Justin brings Maryann's ex-boyfriend, Richard, to the group therapy and the session descends into chaos. Meanwhile, Cybill quits an acting job out of disgust with Hollywood's lack of respect for older women.
Cybill forgot Ira's birthday and, to ease her guilty conscience, then concocts a crazy scheme to kidnap him and surprise him with the perfect gift - courtside tickets for a Lakers game. Maryann and Zoey act as Cybill's accomplices in the kidnapping scheme and successfully complete their mission - only to discover that they've abducted the wrong man. Meanwhile, Cybill's long-lost niece, Claire, visits from Bakersfield and is starstruck with her aunt's glamorous Hollywood. While Cybill entertains Claire, she finds a photo showing her with her brother, a man she never knew - and can't remember.
Jeff convinces Cybill to pretend they're still married to please his sweet but old-fashioned grandmother. While Jeff and Cybill are celebrating their pretend 25th anniversary with grandma, the waiter, who is nervous about telling his parents that he's gay, introduces Cybill as his fiancee. Meanwhile, Maryann and Richard enjoy a romantic vacation in the country until the trip gets sidetracked by a veterinary emergency and Maryann finds herself delivering a calf.
Maryann convinces a reluctant Cybill to go on the blind date with Bruce, who turns out to be an offensive jerk. Although Cybill is repulsed by Bruce's piggish behavior, after a storm straps him at Cybill's for the night along with Maryann, Zoey, Ira and his mother, she is determined to be nice to him after he saves the life of Ira's mother. Meanwhile, Maryann and Dick work on their co-dependency issues, and Ira tries to improve his relationship with his mother.
When Zoey's first love, Gianni, visits from Italy and steals her heart with his good looks, charm and romantic gestures, Cybill suspects he will soon propose marriage. Unfortunately, the seemingly perfect Italian turns out be a cad who makes a secret pass at Cybill behind Zoey's back. After rejecting the overly-amorous suitor, Cybill must decide whether or not to break her daughter's heart and tell her the truth. Meanwhile, Maryann is bent on wreaking cruel revenge on the lecherous Gianni.
Cybill is thrilled when she gets a job hosting a popular morning talk show - until she discovers that her co-host is a prissy, jealous domestic goddess-type who enjoys playing live, on-air practical jokes on Cybill. Adding to her troubles, Cybill finds herself both sexually attracted to and morally repulsed by her deceitful new producer. Meanwhile, Ira stands in as Cybill's best friend and advisor while Maryann goes on a shopping spree in Paris.