Money Out the Window is the fifth episode of the fifth season in this television sitcom on Family Matters, which was aired from ABC on October 22, 1993. It was directed by Gary Menteer and written by Gary M. Goodrich.
Eddie still hasn't gotten over the gambling habit and Weasel and Waldo entice him in their football betting venture (even though Urkel warns him about the risks of gambling since he was the only one who did learn his lesson). When Eddie loses a bundle, a thug named Bones (Bubba Smith) pays him a visit, threatening him with serious injury if the debt is not settled in a timely manner. Refusing to listen to Steve, Eddie sells Carl's precious stamp to settle the debt: a decision he will regret and simply wish Bones beat him up before his father finds out. Meanwhile, Laura adds a night job to her hectic schedule to try to get more money for a car, resulting in her being tired throughout the day. Soon Harriette convinces her to focus on her day job and let them come up with the other half of the money.
Eddie proves he has learned nothing form his previous gambling experiences as he's lured into gambling again by his friends, Waldo and Weasel in football bets. However, Urkel is the only one who learned his lesson the last time they've gambled and warns him about the consequences again should he do so. Steve reminds Eddie of the consequences from the last time they gambled at an illegal casino in Mom's Bakery back in Busted and how they got arrested during the police raid. He also mentions that gambling for football bets are illegal everywhere else except for Las Vegas and on legalized casinos on Native American reservations. Weasel is confident in his system but Urkel is skeptical and demands to know why. He explains that he bets with the football teams whose cities hosted the ugliest women. Despite Steve's admonition against joining in because he knows Weasel will not cover for the losses, Eddie gives in to his greed and ignores Urkel. Meanwhile, Laura is working the graveyard shift at a local coffee house. She wants to buy her own car without having her parents help her out. Unfortunately, her job causes her to be tired every morning and it was being unhealthy for her not sleeping. Pretending to sleep in her bed, Harriette is relieved and closes the door to her room. Once gone, Laura easily sneaks out of her room using the tree next to her room. The next day, Eddie loses a bundle on his bet for the football games and Steve shakes his head, knowing that he had warned him not to go with his friends to gamble again. Then, a tough thug and bookie, Bones pays him a visit at the house. Weasel and Waldo are excused by him right away because they paid up immediately. Bones gives him an ultimatum that if he doesn't pay up by tomorrow, he'll crush him (bone per dollar). Eddie's scared for his own well being that he secretly sells his father's prized stamp "Head of Freedom Statue" for $300 to pay him off, against Urkel's recommendation to go get help from Carl and accept responsibility for his actions. This decision is the one he'll later regret and wished that Bones simply beat him up before his father finds out the truth again. One night, a worried Harriette catches Laura sneaking into her room. She has a heart-to-heart talk about the consequences of endangering her health without sleeping again. Laura tried to convince her that all she wanted to do was buy her own car without her parents helping her out and felt working two jobs can give her that opportunity. Finally, Harriette convinces her to quit her job at the coffee house because her sneaking out at night to go to work without telling her about it is irresponsible of her. She tells Laura to concentrate on her day job and school and let them come up with the rest of money because they love her. The next night, Eddie comes home from his work and learns his lesson the hard way when Carl finds out once again. When he claims he wants to spend time looking at stamps, Eddie finds out that his father knew better. Carl begins his lecture by mentioning that he found about Eddie gambling again and that he sold the "Head of Freedom Statue" stamp(Carl's prized stamp) for $300. When Eddie asks him how he knew, Carl mentions Steve told him the truth about it and that his quick call from Al(the owner of the stamp emporium) backed up Urkel's claims. He is furious with Eddie for forcing him to buy back his own stamp and demanded answers for it. This time, he is forced to confess in gambling again with his friends, Waldo and Weasel, for football bets. Eddie mentions that Steve tried to warn him against gambling from last time when they got busted at an illegal casino but he had ignored it out of greed. He admitted that he lost $300 to a tough bookie named Bones who later visited the house and threatened bodily harm if he didn't pay up. Eddie got scared for his own well being and sold the stamp to get the money to pay the bookie off. Carl asks Eddie why he never came to him for help and confess. Eddie explains that he didn't want to go to his dad for help because he was afraid of being yelled at again like last time when he was caught gambling. Carl pointed out Eddie had made serious mistakes before in gambling and thought his own son would've learned his lesson from last time. Eddie agrees and also admits that he had believed in using Weasel's foolproof betting system. When Carl asks about it, Eddie admits it was for betting for the football teams who cities has the ugliest women. Carl disciplines him for not going to him when he was in trouble and gives him a lengthy grounding. In addition to it, Eddie will have to pay back the $300 that he owes for making Carl buy back his own stamp. Eddie promise he's never going to gamble with his friends again no matter how much money he makes. The father/son moment looking at stamps, is short lived when Steve shows up in his polka outfit with his accordion on his chest. He asks Eddie if he's sure that he doesn't want to go to the polka hall with them. Eddie ask if he convinced someone else to go with him. Urkel says yes and now he has a new polka partner. His partner is revealed to be Bones, whose dressed up in the same fashion as Steve, horrifying the Winslow men. It turns out that the bookie loves polka music and loves going to the hall everyday. He tells Urkel, they should get going because he doesn't want to be late. Both Steve and Bones leave for the polka hall playing their accordions much to the disgust of Eddie and Carl.
- Reginald VelJohnson as Carl Winslow
- Jo Marie Payton as Harriette Winslow (credited as Jo Marie Payton-Noble)
- Rosetta LeNoire as Estelle Winslow
- Darius McCrary as Eddie Winslow
- Kellie Shanygne Williams as Laura Winslow
- Bryton James as Richie Crawford (credited as Bryton McClure, credit only)
- Jaleel White as Steve Urkel
- Shawn Harrison as Waldo Geraldo Faldo
- Bubba Smith as Bones
- This is the second time that Laura is sleep-famished. The first time was in The Way the Ball Bounces.
- This is the third time Eddie was proned to gambling and refused to seek help from Carl. The first time was in Fast Eddie Winslow and the second time in Busted. This would however be broken in Season 7's Scammed.
- This marks the 3rd time Urkel warned Eddie not to do something that is law breaking. In this case gambling in football bets with their friends while underage. The first time was back in Fast Eddie Winslow, the 2nd time in Jailhouse Blues and later Scammed.
- The stamp Eddie sells for money is Carl's prized stamp "Head of Freedom Statue".
- Bubba Smith is the 2nd actor from the Police Academy films to guest star on Family Matters. The 1st being David Graf in An Officer and a Waldo.
- Eddie: Waldo's mom had plastic surgery and I'm invited to her welcome home party.
- Estelle: What did she have done?
- Eddie: A fanny lift. Everyone's hoping it'll stay above her knees this time.
- Urkel: You know, I'm going to hate myself for asking, but what in Sam Hill do ugly women have to do with football?
- Weasel: Think about it, wouldn't you be a lot meaner if you came from a city full of ugly women?
- Urkel: I was right. I hate myself.
- Eddie: Weasel, your betting system bites! We bet on ten games and lost eight of them.
- Weasel: Might I remind you that we also won two games, Mr. Glass-Is-Half-Empty?
- Waldo: Hey, I want an Indian name, too!
- Bones: Come on Steve, we don't want to be late.
- Urkel: A one and a two...
- [Steve and Bones play their accordions and dance their way out of the Winslow home much to the embarrassment of Carl and Eddie.]