Jailhouse Blue is the fifteenth episode of the third season of Family Matters, which aired on ABC on January 24, 1992. It was directed by Gary Menteer and written both by Sara V. Finney and Vida Spears.
Harriette's troublesome Detroit cousin, Clarence (Shaun Baker), is sent to live with the Winslows. He quickly proves to be a bad influence on Eddie and gets him, an unwilling Urkel, and a car full of pretty girls in serious trouble for grand theft auto. Harriette sends an unremorseful Clarence back to Detroit to face his family's wrath after being fed up with his attitude while Eddie is remorseful for his involvement. While the owner agrees to drop the charge against him, Carl still punishes Eddie to do community service by volunteering at elderly shelters.
Harriette and Rachel's troubled cousin, Clarence, is invited to stay with the Winslows for a few months. His family in Detroit apparently has had enough of the boy's growing police record. They hope that one stay with the Winslows will help him become a person of the law and give up on being a thug. However, Harriette immediately regrets letting him stay with them, especially after she noticed that his "bad-boy" attitude is more than they can handle and he becomes a negative influence on Eddie. She's not the only one who dislikes his bad boy persona. Most of the family and Steve dislike his attitude too. Especially after he first met him and tells Eddie how he truly feels about him. He thinks that he won't amount to anything because he's not cool and is going nowhere in life being a thug. Then, Urkel tries to warn his mother to get inside quickly because of his killer bee experiment. During the evening, Mother Winslow stays with the kids as Eddie and Clarence asks for the family car from Carl, for their joyride to pick up girls. Unfortunately, he refuses and tells them to stay away from it. He, Harriette and Rachel leave for dinner and the boys pondered what to do next. Undaunted, Clarence decides to find a car for the joyride more suitable for them, since he believes that the family car would only pick up older women.
Later on in the kitchen, Eddie is working on a puzzle when Steve shows up and invites him to go to the conservatory for the annual BYOB (Bring Your Own Binoculars) night. It isn't long before Clarence shows up in the kitchen and brings Eddie and Urkel in the garage with a Ferrari and two girls named Oneisha and Halawna. He immediately invites both boys along for the ride, claiming that the owner let him borrow the car and that he will immediately return it when they're done. Eddie's willing to go, but Steve refuses to budge and suspects that Clarence had actually stolen the car from the owner by disguising himself as a parking valet. He warns Eddie to think about the consequences ahead if he goes with Clarence on the joyride. Eddie begins to have second thoughts, but ultimately his attractions to the girls causes him to ignore Steve's warning and hop in the car with them, claiming that he's lonely and wants female companionship. Then, Clarence takes a very reluctant Steve with them so he can't tell Carl the truth about what happened. Steve protests to his abrupt hostage situation, but Eddie reassures him that his cousin knows what he's doing and to enjoy the ride. However, it turns out Steve's warnings against going on the joyride were best heeded, after the police quickly put it to an end when they pull the group over and discover that, as Steve had suspected, Clarence had stolen the Ferrari! The boys wind up at the precinct and they're photographed for possible charges of grand auto theft by the owner of the Ferrari.
At the Winslow house, Carl is infuriated with Clarence for bringing Eddie and Steve into his scheme, knowing that he was bad news. He tells Harriette that her relatives in Detroit made a terrible mistake in letting him come to Chicago and he should have been locked up in the first place. Minutes later, Lieutenant Murtaugh shows up with Eddie and Clarence at the house. Immediately, he tells Carl that when he dropped Steve off at the Urkel house, his parents were very upset because he brought him back. He then tells him that he convinced the owner of the Ferrari to drop the charges. Once Lieutenant Murtaugh leaves, Carl starts to lecture Clarence in his usual furious manner and prepares to throttle him. However, Harriette convinces him to let her deal with Clarence and he deals with Eddie, mentioning that if he should kill someone, he should make sure it's a close relative. Carl agrees and orders Eddie into the kitchen immediately and sends Laura to bed, leaving a remorseless Clarence to face an equally angry Harriette in the living room. She immediately lectures him on his attitude and how it has had a negative impact on her son and for forcibly bringing Steve into the mix. Harriette tells Clarence off that he's not cool because of his arrogant attitude and that cool people are responsible, levelheaded and respectful people who know right from wrong, and learn from and admit to the mistakes they make. Unfortunately, Harriette's words are not enough as Clarence only says he's sorry for getting caught and doesn't show any remorse for his actions. Harriette gets so fed up with her cousin's arrogant attitude that she orders him to pack his bags for his return home, and also tells him that she will be calling his mother back in Detroit to inform her of his impending return. Clarence coldly tells her that he does not need her or anyone else telling him how to live his life and storms upstairs to pack.
Alone in the kitchen, Carl is about ready to discipline Eddie for his involvement with Clarence in stealing the Ferrari. Just before he could have a chance to do so, a remorseful Eddie apologizes for his irresponsible behavior and scolds himself. He admitted Steve warned him not to get inside the stolen Ferrari and go on the joyride. However, because Clarence tempted him with pretty girls, he ignored it and learned first hand on how much a negative influence he was after they got arrested ("Nobody looks cool in handcuffs!"). Even though the owner has agreed to dropped the charges and Carl forgives him, Eddie will still have to face punishment. He tells his son that he will not ground him, but he'll be doing community service with the Meals on Wheels Program every Saturday for the next entire year no matter how good or bad the weather is, starting at 6AM, which is only a few hours later, much to Eddie's chagrin. Eddie heads off to bed as Harriette comes into the kitchen. Harriette reveals that her talk with Clarence didn't go well because he arrogantly refused to see the error of his ways and that it was like talking to a wall. She reveals that they are sending him back to Detroit for him to face proper punishment from his parents. However, Harriette still worries about Eddie meeting future temptations and repeating himself. Carl reassures her that he won't because Eddie knows that what he was about to do is a serious offense.
Steve tells Laura about his experiences being in jail with Eddie and Clarence, but she shoves him out the house and tells him to go back to his own house.
- Reginald VelJohnson as Carl Winslow
- Jo Marie Payton as Harriette Winslow
- Rosetta LeNoire as Estelle Winslow
- Darius McCrary as Eddie Winslow
- Kellie Shanygne Williams as Laura Winslow
- Jaimee Foxworth as Judy Winslow
- Bryton James as Richie Crawford (credited as Bryton McClure)
- Jaleel White as Steve Urkel
- Telma Hopkins as Rachel Crawford
- Shaun Baker as Clarence Baines
- Vivica A. Fox as Halawna
- Mari Marrow as Oneisha (as Mary Marrow)
- Murtaugh repeats his "Keep it moving, Mr. Backwards Hat" line in this episode. The first time was in "Born to Be Mild".
- Lt. Murtaugh: I dropped the, uh, nerd off next door at the, uh, nerd house. His parents were very upset.
- Carl: Why, because he was in jail?
- Lt. Murtaugh: No, because I brought him back.
- Harriette: Clarence, are you sorry for any of this?
- Clarence: Yeah. I'm sorry I got caught.
- Harriette: Okay. I've given you every opportunity. Get upstairs and pack your bags. You're goin' home.
- Clarence: What? You bluffin'.
- Harriette: No, I'm not. Get upstairs and get your stuff, Clarence! I'll call your mother and tell her you're on your way.
- Clarence: [offended] Fine! I don't need you, cousin.
- Carl: Now, first of all...
- Eddie: I can't believe what I did. It was like, who is that person? I actually let Clarence convince me we were only borrowing that car.
- Carl: Well, it was wasn't borrowing...
- Eddie: It was stealing.
- Carl: Uh-huh. Mm-hm.
- Eddie: Dad, I thought Clarence was so cool.
- Carl: Yeah, well...
- Eddie: But he's not cool. Nobody looks cool in handcuffs.
- Carl: You're right. Now, Edward, if you just let me...
- Eddie: I am so disappointed in myself. I let myself down, and worst of all... I let you down.
- Carl: Well, that's right.
- Eddie: Thanks for the lecture, Dad. I really learned my lesson.
- Carl: Well, I'm sorry I had to be so rough on you.
- Eddie: Hey, I deserved it.
- Carl: You're going to be volunteering your services every Saturday for the next entire year for the Meals On Wheels program.
- Eddie: Every Saturday?
- Carl: Rain or shine. Starting bright and early 6 a.m. tomorrow morning.
- Eddie: But that's only five hours from now.
- Carl: Well, you better get some rest then.