Judging Amy is an American legal drama television series that was telecast from September 19, 1999, through May 3, 2005, on CBS. This television series was produced by Barbara Hall/Joseph Stern Productions, CBS Productions and 20th Century Fox Television and starred Amy Brenneman and Tyne Daly. Its main character (Brenneman) is a judge who serves in a family court for the Connecticut Superior Court's Hartford district; in addition to the family-related cases that she adjudicates, many episodes focus on her experiences as a divorced mother and on the experiences of her mother, a social worker in the field of child welfare. This series was based on the life experiences of Brenneman's mother.

Plot Amy Gray, an attorney and Harvard University graduate, moves back to her hometown of Hartford, Connecticut after separating from her husband Michael in New York City. She and her six-year-old daughter Lauren move in with her widowed mother, Maxine Gray who is a caseworker for the Connecticut Department of Children and Families. The move back to Hartford also reunites Amy with her two brothers. Her older brother Peter juggles the operations of their late father's insurance company along with the struggles he and his wife Gillian are facing towards starting a family due to fertility issues. At the same time, Amy's younger brother Vincent an aspiring writer, struggles to jumpstart his career while working odd-end jobs. Later on, Amy's cousin Kyle McCarthy, a former med student, returns to help cope with the rehabilitation of his drug addiction. In her line of work Amy takes on a wide variety of challenging cases, with the assistance of her Court Services Officer Bruce van Exel and Court Clerk Donna Kozlowski both of whom she ultimately becomes good friends with. In the de facto series finale (the series was canceled after the conclusion of the season) Amy quits the judiciary to run for the U.S. Senate.

Characters Character Actor Season123456 Amy Gray Amy Brenneman colspan="6" Vincent Gray Dan Futterman colspan="3" colspan="1" Bruce Calvin van Exel Richard T. Jones colspan="6" Gillian Gray Jessica Tuck colspan="6" Peter Gray Marcus Giamatti colspan="6" Lauren Cassidy Karle Warren colspan="6" Maxine Gray Tyne Daly colspan="6" Donna Kozlowski Jillian Armenante colspan="1" colspan="5" Kyle McCarthy Kevin Rahm colspan="3" Sean Potter Timothy Omundson colspan="4" colspan="1"

Main

Judge Amy Madison Gray, played by Amy Brenneman: After separating from her husband, Amy Gray returns to her childhood home with her daughter, becomes a judge on Connecticut's family court, gets a divorce, and tries to get on with her life. Balancing her new job, her family, and trying to rebuild her love life is not easy, but she keeps trying. She makes a name for herself in family court for her unusual methods and sentences and her stubbornness, which sometimes gets her in trouble. She dates several men. Her longest and more serious relationships are with lawyer Stuart Collins and David McClaren. Amy and Stuart dislike each other at first, but when she asks him to be Eric Black's lawyer, they get closer and eventually get engaged. However, Amy leaves him at the altar on their wedding day, saying he has a way of always convincing her to do things she does not want to do, calling him "a bully". She meets David McClaren during her short stint in the criminal court, and things are rocky from the start. Amy becomes pregnant by him and they plan to marry, but things fall apart when she miscarries and they part ways soon thereafter. In the last episode of the series, she quits the judiciary to run for Senate, to try to prevent the passage of a law that will effectively end the juvenile justice system by allowing the State's Attorney's office to try teenagers as adults at their own discretion. Amy's often complicated and ever changing definition of a relationship with her Court Services Officer, Bruce Van Exel, whom she calls her "best friend" and with whom she's shared intimate moments – despite his refusal to date white women, ends with him coming to be with her in Washington as she testifies at a Senate Hearing. Maxine McCarty Gray, played by Tyne Daly: She is Amy's widowed mother. A social worker for the Department of Children and Families, she had retired, but she returns to the job at the start of the series. She is willing to do whatever it takes to help the children in her care, even bending the law. She is an opinionated, strong-willed woman, very set in her ways, and capable of holding long grudges (she has not spoken to her brother in over 12 years), but loving to her family. Her relationship with daughter Amy is often not easy, since they are so much alike. After a troubled courtship, she becomes engaged to a wealthy businessman, Jared Duff, but he dies 48 hours before their wedding (a storyline twist necessitated by the unexpected death of the actor Richard Crenna, who played the character). She later becomes involved in a very complicated, on-again off-again relationship to her landscape designer Ignacio Messina. She suffers two heart attacks in the last season and has to undergo open heart surgery, but makes certain lifestyle changes and recovers well. At the end of the series she accepts Ignacio's marriage proposal and is set to retire again, becoming a foster parent to the last child she helped. Vincent Gray played by Dan Futterman (seasons 1–3 & 6; special guest season 5): He is Amy's giftedSeason 2 episode 5 "Unnecessary Roughness" younger brother, with whom she has always been closest. Vincent is the winner of a Pushcart Prize during college, but then went on a backpack tour of Europe because he was overwhelmed with the expectations for success. He later writes a novel titled A Fortunate Son, about a Rabbi and his son. He sells the rights to this book to a movie company, who he says are going to turn the Rabbi and other characters into walk-ins. He's torn about giving up his characters and turns to his sister Amy, who advises him to "take the money and run", given that he is about to move to San Francisco with his new wife. He later gets a deal for a collection of short stories, but is unable to meet the deadline after the emotional stress of his divorce and he had to give back the considerable advance ($15,000) that he was paid. At the beginning of the series, he is roommates with a man with whom he owns a dog-washing business. When his roommate gets married, he becomes roommates with Donna, with whom he later becomes best friends. As he attempts to continue his writing career, he holds a number of jobs: dogwasher, reporter, and freelancer. He eventually marries his girlfriend, Carole Tobey (Sara Mornell), who has breast cancer, and leaves with her for San Francisco. The impending move causes Amy to become angry with Vincent, but when Amy finds out about Carole's breast cancer, she makes amends with him, gives him legal advice on his movie deal – even giving him the family's good luck talisman "the Surfing Monkey" at the airport. He comes home briefly when his mother calls and asks him to come help Maxine and Amy patch things up – as a fight has resulted in Amy moving out with extreme tension existing between mother and daughter. Because of Vincent's visit, Amy buys the family home, Maxine becomes a renter, and the family is put back together. Sometime later, his cousin Kyle arranges for him to arrive as a surprise to Amy's wedding to Stuart Collins. The wedding never happens. He returns home permanently soon after, explaining that Carole has left him for her oncologist. He later explains that this was because he couldn't "be there" for her in the way that she needed him to be while her doctor could. Stuck after his book deal is canceled and he is in debt to the publishing company, he starts driving for the Department of Social Services, then gets a job at a teen center. When a teen is shot in front of him, his boss goes on a bender and realizes she's "addicted" to Vincent and gets him a job teaching writing at a Maximum Security Detention Center. Vincent seems to attract bad luck – he gets shot while helping a woman being mugged in a grocery store parking lot, then later gets blown up and loses his ability to walk and read. Peter Gray, played by Marcus Giamatti: He is Amy's older brother. He inherited the family business from his father and he is good at it, even if he wasn't given a choice. He is a good man who sometimes surprises people with some outbursts. He and his wife Gillian have been trying to start a family for several years, but their inability to have children of their own leads to them pursuing adoption. Through their adoption agency, they are chosen by a pregnant woman named Evie as adoptive parents to her baby. She gives birth to a boy who Peter and Gillian name Edward, after Peter's late father, but call him Ned for short. Shortly after Ned's adoption is completed, Evie returns and reclaims her son after Ned's biological father reemerges, but ends up returning him to Peter and Gillian after her arrangements don't work out. Sometime after adopting Ned, Gillian gets pregnant and gives birth to another son, Walt. Things get rocky after Walt's birth and they separate for a while, even dating other people. Peter goes through a "rebellion" phase, trying to recall his teenage dreams, until he finds out his business is almost bankrupt. Soon after, he reconciles with his wife. Gillian Gray, played by Jessica Tuck: She is Peter's wife. A high strung controlling woman with a good heart, she completely loves her husband. She is usually well-meaning, but also often obsessive and nerve-wracking. After being unable to get pregnant, they adopt baby Ned. Sometime later, however, she gets pregnant, but things go wrong during the delivery of Walt, and she falls into a coma for a while. She and Peter have problems soon after (and she dates another man) but they reconcile. Lauren Cassidy, played by Karle Warren: She is Amy's daughter, six years old at the start of the series. A mostly well-adjusted girl, she is going through the pains of childhood and preadolescence with divorced parents, but a loving family. She struggles over her father's relationship with his new girlfriend Leesha, whom she likes at first. When Lauren is 12, her uncle Peter takes her for her haircut and she returns home with her long straight hair cut into a hipper, shoulder-length cut. Her boyfriend Victor turns out to be the son of one of her mother's later boyfriends, David McClaren, which causes Lauren to feel awkward and disgusted. When Amy becomes pregnant with David's child, Lauren reveals what a total blow to her social life this will be and is furious. She later becomes accepting and supporting of her mother after she miscarries. Toward the end of the series, Lauren begins to hang out with a group of friends who embrace the straight edge culture, which puts her at odds with her mother. Kyle McCarty played by Kevin Rahm (seasons 3–5; special guest season 6): He is Amy's cousin, the son of Maxine's estranged brother Richard (William Devane). He is a former medical student who was expelled because he was addicted to Dilaudid. Shunning his father, he comes to his aunt Maxine for help. She gives him a home and gets him a job as a counselor at a facility for runaway teens. He later moves in to share a flat with Donna after Vincent leaves and finds a hospital willing to give him a new chance to finish his medical residency, and gets into a complicated on/off relationship with fellow doctor Heather Labonte, as well as fighting an attraction to his supervisor, Dr. Lily Reddicker. After his father dies, he quits his job and finds a new path in life as a medic with the SWAT unit. He finally decides to accompany his ex-girlfriend Heather to Minnesota and take care of their son while she is in rehabilitation.