Throughout the first two seasons, Dylan's relationship with Brenda helps him through several traumatic events, including his struggle with alcoholism and his father's arrest (and eventual conviction) for several white-collar crimes. However, when Dylan takes Brenda to Mexico against her father's wishes, her father forbids her to date him. Brenda refuses to obey and moves in with Dylan, who becomes increasingly unhappy in the relationship since his feud with Jim. Their new living arrangement annoys Dylan to the point of him nearly ending their relationship. At this point, Jim proposes to send Brenda to France for a French immersion program (in Kelly's place) for the duration of the summer.
With Brenda in Paris, Dylan starts spending a lot of time with Kelly by helping her babysit her little sister and entering a doubles beach volleyball tournament with her. The two have a strictly physical affair, but Kelly ends it out of loyalty to Brenda. Upon returning from Paris, Dylan and Brenda reunite. This doesn't last long though, as Brenda (who also has an affair) runs into the guy she was seeing in Paris at a video store and starts seeing him behind Dylan's back. Dylan and Brenda break up, and Dylan heads straight for Kelly. This doesn't last long either, because Brenda, upon seeing them on a date, gets mad at them, causing them to take a step back from their potential relationship. Dylan, frustrated with the situation, takes a road-trip to get away from them. When he returns, Kelly and Brenda tell him to make a choice. When Brenda is unable to show up when he invites both girls to see his father, he decides to choose Kelly.
When Dylan's father is prematurely released from prison, Kelly helps Dylan re-establish a healthy relationship with his father. However, this does not last long; Jack is killed by a car-bomb planted by the mob because he could not pay a debt.
Dylan spends the remainder of the third season managing his relationship with Kelly, and graduates from West Beverly High School with the rest of his friends in the season finale.
In the fourth season of the show, Dylan meets a woman, naming herself Suzanne Steele, who claims to be the mother of Jack McKay's illegitimate child, a young girl named Erica (Noley Thornton). Dylan is initially skeptical, but eventually accepts them as family. This, coupled with Dylan's close friendship with Brenda, strains his relationship with Kelly. They repeatedly break up and get back together, but they ultimately call it quits after a bad fight. Dylan briefly reconciles with Brenda before she leaves for London.
After Suzanne begins dating an enviromental chemist named Kevin Weaver, whom Suzanne soon marries, Dylan then agrees to help fund Erica's new stepfather's personal project, which promotes clean beaches (a cause Dylan is passionate about). It is revealed to the audience (but not to Dylan or anyone else) in the season finale that they have been conning him this whole time, and uses his cause (and longing for family) to steal his large trust fund.
The show's fifth season is set several months later. Dylan, nearly bankrupt because of the events of the previous season, has suffered a relapse and spent the summer in Mexico, mulling over issues with Brenda, Kelly and the betrayal of his "family". Alienated with his life and life in general, Dylan keeps his financial situation a secret from everyone. After Dylan returns to Beverly Hills, he finds out that Brandon and Kelly have started dating and makes a scene at Donna's Cotillion rehearsal dinner. He mocks Kelly, who in her anger tells him that "we are so over".
Dylan then starts taking drugs, and starts sleeping with Valerie Malone, who discovers his secret about his drug problem and of his true financial situation and informs the rest of Dylan's friends. Yet, he continues in his downward spiral, until his friends hold an intervention. He agrees to go to rehab, but checks out after only one day. He then loads up on drugs and gets into a life-threatening car wreck, where (while fighting for his life) he has a series of dream about his innocent half-sister Erica, and realizes that he must clean himself up in order to save her from her evil mother Suzanne and Suzanne's partner-in-crime Kevin. Afterwards, Dylan checks back into rehab, and beats his demons once more. After he is released from rehab with most of his confidence and self-esteem back, he redoubles his efforts to track down Erica and her mother and stepfather. With an investigator named "Jonesy" (and Valerie's help), they track down Kevin and Suzanne, whom are hiding out in Mexico, and after a caper, recover Erica and all of Dylan's money.
A short time after, he starts hypnotherapy in order to research a role for a screenwriter friend's (who was also in rehab) next movie. In the process of this, he discovers a past life which reveals Kelly to be his soulmate. This news, despite Kelly's ongoing relationship with Brandon, sends Dylan to confess his continued love for her. He offers her a trip around the world with him. Brandon is threatened by Dylan and proposes to Kelly, forcing her to make a choice between the two. Her answer, that "she chooses herself", became one of the shows' most quoted and famous lines. Kelly chooses neither, as she loves and would always love them both. It is later said that she refuses to choose between them, not because she can't choose, but because it would destroy their friendship, similar to how it damaged hers with Brenda.
During the show's sixth season, Dylan finds out who the FBI believes killed his father, a mobster named Anthony Marchette, and decides to seek revenge. He uses the mobster's daughter, Toni Marchette to get close to him, but soon finds himself falling in love with her. Despite Dylan's feud with the mobster (to whom Toni is very close), the two eventually decide to get married and relocate to Hawaii, which results in Toni's father ordering a hit on Dylan to prevent it.
The hitmen end up accidentally killing Toni, who is driving Dylan's car in a bad rain storm at the time of the hit. Dylan, distraught over his wife's death, is given a gun by Anthony Marchette and asks Dylan to kill him. Dylan refuses, harshly telling him that "My father is gone, your daughter is gone. We're even now. The killing is done." It is later revealed that Marchette kills himself shortly after that exchange. Immediately after, he leaves town on his motorcycle, taking the stray cat Toni had adopted with him.
Several months later, in the sixth season two-part finale You Say It's Your Birthday, Donna sends an e-mail to Brenda looking for a video birthday message for Steve. She instead gets a letter from Dylan wishing Steve a happy birthday. Some time after his departure from Beverly Hills, Dylan had reconciled with Brenda and moved into her London apartment.
Shortly after his surprise return to Beverly Hills during Thanksgiving in 1998, he also sells his Porsche and burns all the money he receives from the sale since Toni died in it. He also reveals that he sold his house.
During seasons 7 and 8, although Dylan does not appear at all, it is believed that he and Brenda are still together, considering that Kelly and Brandon intend to visit them while they are on their honeymoon.
However, it is later revealed that Dylan flew back from London to attend Kelly and Brandon's wedding, but left without anyone seeing him because he couldn't stand to watch Kelly marry another man. It is also believed that he broke up with Brenda just before this, because he remarks in season 9 that he hadn't been with Brenda in over a year.
In season 8, Brandon and Kelly run into Dylan's half-sister Erica on the street. They find out that she ran away from Dylan's mom in Hawaii and is prostituting herself. After helping her work through her issues, Kelly sends Erica to London to be with Dylan.
Dylan returns to Beverly Hills towards the beginning of the ninth season, apparently because he misses his home and friends, although he admits to Kelly that he misses her especially. He also relapses and is once again on heroin (however, all references to his alcoholism are absent and he is frequently seen drinking alcoholic beverages in casual, social situations). After failing to win Kelly back, he starts dating the new bad girl Gina Kincaid, despite obviously still being in love with Kelly. Dylan and Kelly battle a mutual attraction, despite being in on-and-off relationships with Gina and Matt Durning respectively. This is especially noticeable when Kelly blames Gina and others for Dylan's drug problems (as with the case back in Season 5 with Kelly blaming Valerie for Dylan's drug problems), and gets Steve to take the credit for a heroic act (in Dylan's stead) to avoid having anybody know that she and Dylan were out together.
In the show's final season, Dylan finds out that his father faked his death and is in the Witness Protection Program. After being furious that Jack has let Dylan think his father was dead for seven years, he later accepts that it was the right thing to do when news of Jack's survival quickly makes its way to unfriendly ears. Dylan's relationship with Gina also ends when, upon considering leaving Los Angeles with her, he finally admits that he's still in love with Kelly and can't leave.
In the two-part Series Finale The Penultimate & Ode To Joy, Dylan and Kelly reunite at David Silver and Donna Martin's wedding with a kiss.
Dylan is revealed as the father of Kelly's son in the third episode. In episode 6, Dylan calls Brenda while she is talking to Kelly and Ryan. When Kelly finds out it's Dylan on the line, she talks to him. It turns out that Dylan wants to try and be a family again with her and Sammy. However, this would mean they would have to move out of Beverly Hills. After much thought, Kelly breaks up with Ryan, as she said that she needs to try to work things out with Dylan even if they may not work. Ryan hurt, tries to get her to stay. He asks Kelly about the reason Dylan would call Brenda's phone, not hers. Fearing Brenda and Dylan and secretly back together, she confronts Brenda. She asks Brenda if there is a relationship going on between her and Dylan, and criticizes Brenda for taking her "seconds" (which Kelly is mistaken, as Dylan dated Brenda first before he dated Kelly). After hearing Brenda say that her and Dylan's relationship is platonic, Brenda and Kelly make up. Kelly decides to try to repair her relationship with Dylan while Brenda sadly deletes his number from her phone. It is implied that there may have been more to the story of Brenda and Dylan's relationship that she didn't share with Kelly as she shed some tears when she deleted his phone number.
While Dylan is widely considered a fan-favorite character of the show's ten-season run, he was also the most controversial. His season six departure is considered by some fans to be the point where the show jumped the shark, and many derided it for being too unrealistic and not consistent with the Dylan character, citing his previous unresolved fear of commitment as a reason why his whirlwind marriage to Toni Marchette didn't make canonical sense.
Also controversial was his season nine return, and his unacknowledged use of alcohol. Canon dictates that Dylan was a recovering alcoholic, and his friends had all known, yet he was often seen drinking in the company of his friends with no mention at all of his addiction. This was later retconned, when he was asked about his past abuse. His answer, that he could drink in moderation, was heavily criticized for being insulting and unrealistic.
When the Dylan character was first proposed as a series regular, Fox didn't like him and didn't want him for more than a story arc. Executive producer and TV mogul Aaron Spelling disagreed with Fox, and instead of doing away with the character, opted to pay Luke Perry's salary himself for the first two seasons of the show. Fox changed their tune after the character's steadily growing popularity and Luke Perry's emergence as a teen idol.
PERRY CONFRONTS PERIL FACE TO FACE : IN CHILLING `INVASION,' `90210' VETERAN FINDS HIMSELF BETWEEN SPACE ROCK, HARD PLACE.(L.A. LIFE)
May 03, 1997; Byline: Keith Marder Daily News Television Writer So, how long does it take to make Luke Perry ugly? About two hours. Perry goes...