The character began as Cosmo Kramer's lawyer on Seinfeld. Chiles is a parody of famed attorney Johnnie Cochran; both are bespectacled, mustachioed, well-dressed, African-American lawyers with the same initials and penchants for grandiose vocabulary. Morris also emulates Cochran's distinctive enunciation and delivery. After appearing in several episodes during the series' later years, Chiles, along with many other minor characters from the show's past, appeared again in the program's finale and was crucial in failing to achieve acquittal of the characters on charges of violating the Good Samaritan Law. Jackie's catchphrase is "I am outraged!" Some have commented that the real-world persona of attorney Cochran was so flamboyant Morris had to do little more than mimic him directly in order to have a successful character who is, in reality, more impersonation than caricature.
- “The Maestro” — Kramer sneaks a cafe latte into a movie theatre and burns himself while trying to climb over the legs of another patron (an obvious satire of the 1994 lawsuit Liebeck v. McDonald's Restaurants) as seen in The Postponement. After describing this as "outrageous, egregious, preposterous," Chiles tells his secretary Suzie to get a cafe latte with a top on it from Java World while also arranging for Kramer to be checked out by Dr. Bison. Following an unseen appointment with Dr. Bison, Kramer was in a taxi cab as Jackie quotes "You put the balm on? Who told you to put the balm on? I didn't tell you to put the balm on. Why'd you put the balm on? You haven't even been to see the doctor. If your gonna put a balm on, let a doctor put a balm on." Kramer told Jackie that his maestro friend Bob Cobb told him to put on the balm where Jackie considers this a public humiliation. The Java World coffee company offers a settlement of a lifetime of free coffee at all of their stores throughout North America and Europe. Kramer accepts the offer before the executive had finished speaking and mentioned any money. While in the taxi, Jackie lets Kramer have it by quoting “I'll take it! I’ll take it! Who told you to take it? I didn't tell you to take it! and then adds in "I know the maestro didn't tell you to take it, he wasn't there.” Jackie stated that he has never experienced anything like this in 20 years.
- “The Caddy" — Jackie sues Oh Henry! candy bar heiress Sue Ellen Mischke for allegedly causing Kramer personal injury due to an automobile accident at the time she was wearing a topless bra. Kramer is distracted while driving when he sees Mischke walking the streets of New York City wearing only a topless bra. While stating that Sue was flouting society's conventions, Chiles describes her actions as "lewd, lascivious, salacious, outrageous!" Chiles even sets up Kramer with an appointment with Dr. Bison. Jerry Seinfeld was present at the trial and told his story upon being reminded by Jackie that he is under oath The lawsuit fails when Kramer demands she try on the topless bra to prove it is hers at Stan the Caddy's suggestion. It fails to fit because she tries donning it over a leotard much to Jackie and Elaine Benes's dismay. Jackie yells at Kramer "Damn fools! Look at that! We got nothin' now, nothin'! I've been practicing law for 25 years, you're listenin' to a caddy! This is a public humiliation! You can't let the defendant have control of the key piece of evidence. Plus, she's trying it on over a leotard, of course a bra's not gonna fit on over a leotard. A bra gotta fit right up a person's skin, like a glove!" (an obvious parody of the O.J. Simpson trial).
- “The Friar's Club” — Kramer's experiment with polyphasic sleep causes him to fall asleep during sex. His Italian girlfriend Connie thinks he has died and gets some friends to dump him in the Hudson River. When he comes to, Kramer accuses her of trying to murder him. During the credits, Kramer arrives at Connie's apartment with two police officers where they arrest her and allow her to call her lawyer. Connie calls her lawyer to meet her at the police station. Her lawyer just happens to be Jackie. Upon hearing that Kramer is one accusing her of murdering him, Jackie says "I don't want nothing to do with it!" Jackie then hangs up.
- “The Abstinence” — Kramer's face ages prematurely when he turns his apartment into a smoking lounge. Kramer then consults with Jackie about filing suit against the tobacco companies for his disfigurement which Jackie states that he's been wanting a piece of them for years. When Kramer asks if he has a case, Jackie replies "Your face is my case." Jackie and Kramer then meet with a tobacco company lawyer Mrs. Wilkie, who alleges that Kramer's face gives him a sense of "rugged masculinity." Jackie replies, "Rugged? The man's a goblin. He's been exposed to smoke for four days. By the time this case gets to trial, he'll be nothing more than a shrunken head." After the lawyer says she will have an offer to settle out of court the next morning, Jackie tells Kramer "Jackie's cashing in on your wretched disfigurement." Kramer settles the case without Jackie's knowledge when he asked Kramer who told him to have the pow-wow. The settlement they see is a Marlboro Man-style billboard in Times Square featuring his own face. Jackie dubs this "the most public yet of [his] many humiliations."
- “The Comeback” — Although Jackie does not appear in the episode, Kramer reveals to Jerry that Chiles has put a restraining order on him, barring him from coming within 200 feet of his office. Kramer goes on to explain that because of this, he could not give Jackie a Christmas gift.
- “The Finale” — At his office, Jackie was scolding a delivery person for putting the cheese on his sandwich when he didn't order for it. After getting a call from Jerry, Jackie represents George, Elaine, Jerry and Kramer when are arrested by Officer Matt Vogel for violating the Good Samaritan law by not coming to the aid of Howie when he was being publicly robbed. He tells Suzie to cancel his appointment with Dr. Bison while packing him a bag for his trip to Latham County. Before the trial, he met with Jerry, Elaine, Kramer, and George Costanza where he scolded George for not wearing the cardigan (George claimed that the cardigan made him look older), has Suzie give Jerry one of Jackie's ties, states that Elaine is looking good, and stats that Kramer is genuine. When the trial starts, Jackie states that the trial is a waste of the taxpayer's money while also mentioning that his four clients barely survived a potential plane crash, that the real criminal is still at large, and that bystanding is not illegal with the locals wanting to create the "guilty bystander." An extended scene had Jackie mentioning that he can get the pilot of the plane in question down to the courtroom to testify on their behalf. When Sidra Holland (from "The Implant") was called to the stand, Jackie developed a crush on her. While the jury was out deciding on the verdict, Jackie was seen sleeping with Sidra where he claims to her that the deciding might take days. He gets a call stating that the jury has reached a verdict which ruins their time together. Despite losing the case, Jackie gets some satisfaction with Sidra, which would have been more satisfying if the jury had not reached a decision so quickly. Before he leaves with Sidra, his last line in the series is the same as Sidra's line about her breasts from the aforementioned episode: "And by the way: they're real, and they're spectacular!"
Notes about Nothing
- Since the end of Seinfeld, the character has appeared in a series of television commercials.
- In 2010, Chiles returned in a series of videos for Funny or Die. He explains it is nobody's business where he's been for the last 12 years.
- In 2013, Chiles was called in by Jim Bean to sue the bears for stealing their Jim Bean Honey. He describes their actions as "egregious, despicable, criminal." This led to a commercial that details Chiles suing the bears.
- Morris planned to star as Chiles in a spin-off, but the pilot never came to be. Though, NBC executives say a pilot was never discussed with them.
- Morris originally had a scene filmed for The Non-Fat Yogurt playing a Dinkins aide if Mayor Dinkins won the election. When he lost, the scene was not used. Jerry Seinfeld has stated that if Dinkins had won, then the character of Jackie Chiles may not have been made.
- Phil is the son of the late Greg Morris, a fellow actor.