Stanley has two children from his first wife Cathy, namely Olivia and Mason. He is a businessman who started a mattress store store with a friend named Norman, but wanted to branch out to other business eventually founding the multi-billion dollar company Walker, Inc.
During the 80s, he met Karen Delaney and quickly fell in love but they decided not to act on it since he was still married. Ten years later, the two officially started a relationship after Stanley got divorced, and he became Karen's third husband. Through Karen, Will's firm Doucette & Stein was hired by Walker, Inc. as legal representation.
Although Karen usually implies that he married Stanley for his money, she has confided in Will (as well as shown during a flashback episode) that she has also fallen in love with him and sincerely cherishes their relationship. She mentions that they have a standing lunch once a month so she can remember what he looks like in the daylight.
Arrest & Imprisonment
During the fourth season, Stanley gets arrested for tax evasion. While in jail, he uses his library time to engage in insider trading which eventually cost him his conjugal visits with Karen. He eventually allows Karen to have affairs with other men so she can be sexually satisfied while he is in prison. She however refuses to at first but on the day she decides to sleep with rich bachelor Lionel Banks, Stanley gets out of prison and comes home.
Just as Karen is about to confess almost having an affair, she ironically catches Stanley cheating with his mistress Lorraine Finster, a worker at the prison cafeteria whom he became involved with months prior to being released. Karen moves out of their mansion shortly and files for divorce, during which Will represents Stanley in court.
Divorce and "Death"
While their divorce is being settled, Rosario breaks the news to Karen that Stanley died of a heart attack while having sex with Lorraine. On his will, Stanley gives Will and Jack $20,000 for them to get married; Grace, a life-sized oil painting of Karen; Rosario, $10 million to be paid after 20 more years of service to Karen (i.e. in 2023); and the rest of his fortune solely to Karen. His cremation took four days which Karen says used so much power that all of Bergen County lost their air conditioning. Stanley's remains were put in two 5-gallon popcorn tin cans and scattered at the Caribbean.
During the eighth season two years after his funeral, Stanley's friends and family find out that he is alive and has been living in seclusion under the witness protection program. Rosario admits knowing about it and that she has been sending him updates on Karen ever since he staged his death to protect him from the mob with the help of CIA agent Malcolm Widmark. Karen feels betrayed by Stan and could not forgive him, eventually starting a relationship with Malcolm instead.
Being an unseen character, Stanley's physical appearance is based solely on the other characters' description of him. He is described as extremely overweight (300lb to 700lb) that Karen often mentions them doing bizarre things to accommodate the massive space he occupies. It is also mentioned that Stanley has become a profitable client of fast food joints Taco Bell and Pizza Hut. She also describes him as "a doughy thing with squat little legs and a bad case of recurring psoriasis". It is also mentioned that he wears a toupee which he never washes. Stanley plays the harmonica and Karen has implied that he has a high-pitched voice.
Stanley's arms are briefly seen in season premiere of season three when he tries to touch Karen's breasts in front of Will. His silhouette is also seen when Karen visited him in jail on Thanksgiving during the fourth season.
- The cast has stated in interviews they envisioned Marlon Brando to portray Stan if he eventually appears. Brando however died in 2004, during the show's sixth season.
- Stanley's favorite perfume is roast beef and lamb chops. Rosario mentions that he eats a hoagie sandwich before going to bed.
- Karen mentions that Stanley's usual breakfast is "two poached deer and a half a grapefruit".
- During Stanley's funeral, Will mentions that Stanley loves knock-knock jokes and Jack says Stanley is a surprisingly good dancer. He plays the harmonica.
- Secrets and Lays
- Went to a Garden Potty
- Tea and a Total Lack of Sympathy
- William, Tell
- Crouching Father, Hidden Husband
- A Buncha White Chicks Sittin' Around Talkin'
- ...And the Horse He Rode in On
- It's the Gay Pumpkin, Charlie Brown
- I Never Cheered for my Father
- Christmas Break
- Lows in the Mid-Eighties
- Steams Like Old Times
- Moveable Feast
- Will on Will & Grace
- Grace in the Hole
- Partners 'n Crime
- Steams Like Old Times