Quagmire is a character from the animated television series Family Guy, known for his extreme behavior and outrageous antics. He is often depicted as a hedonistic womanizer, with a strong preference for younger women and a general lack of emotional depth. Quagmire's over-the-top behavior and inappropriate comments have made him a fan favorite character in the series, and he is often used for comedic relief.

Despite his often offensive behavior, Quagmire does have moments of vulnerability and occasionally shows a softer side. However, these moments are few and far between, and the character is generally portrayed as selfish and amoral. While some viewers may find him hilarious, others may be put off by his offensive comments and actions. Regardless, Quagmire remains an integral part of the "Family Guy" universe and a popular character among fans of the series.

14 "Quagmire's Mom" (S13, Ep10)

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"Quagmire's Mom" is a funny episode of Family Guy that explores Quagmire's backstory a little. The humor in the episode comes from the absurdity of Quagmire's childhood, in which his mother's promiscuous behaviour allegedly contributed to his own sex addiction.

The episode's humor also comes from the dynamic between Quagmire and his mother, who is depicted as a stereotypical "cougar". However, as the episode progresses, she becomes more sympathetic and likeable as it's revealed she's embraced Christianity and tries to make amends with her son. Overall, "Quagmire's Mom" is a clever and funny episode that balances crude humor with more nuanced character development. It also serves as a commentary on the relationship between sex and morality, and the potential for personal growth and redemption.

13 "The 2000-Year-Old Virgin" (S13, Ep6)

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In "The 2000-Year-Old Virgin," Quagmire plays a prominent role as he becomes obsessed with the idea of seducing a woman who has taken a vow of celibacy. Quagmire's attempts to win her over with his charm and sexual prowess provide some of the episode's funniest moments.

Quagmire's character is known for his wild and inappropriate behavior, and he often finds himself in awkward situations due to his sexual obsession, and this episode is no different. Quagmire's pursuit of the celibate woman leads him to join a religious order and take a vow of celibacy himself, which provides even more comedic moments. Quagmire's role in "The 2000-Year-Old Virgin" and his relentless pursuit of his goals creates yet another memorable episode of the Family Guy series.

12 "Herpe, the Love Sore" (S12, Ep16)

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In "Herpe, the Love Sore," Quagmire provides some of the episode's funniest moments as he reacts to Brian's situation with herpes. Quagmire is known for his wild and inappropriate behavior, and this episode is no exception.

Quagmire's reactions to Brian's predicament range from disgust to concern, and his sarcastic comments and witty one-liners add to the episode's comedic value. He also provides some much-needed levity to the sensitive topic of sexually transmitted infections. Additionally, the episode features a subplot involving Quagmire and his obsession with Tinder, a popular dating app. Quagmire's experiences with the app, such as his disastrous date with a woman who turns out to be a prostitute, provide more laughs and add to the episode's comedic value.

Related: Family Guy Characters Voiced by Seth MacFarlane, Ranked

11 "A Fistful of Meg" (S12, Ep4)

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"A Fistful of Meg" is an episode that features the character of Quagmire in a supporting role. The episode centers around Meg, who becomes the target of bullies at school and decides to learn self-defense.

Quagmire appears in the episode as Meg's self-defense instructor and the episode includes several hilarious moments, such as Quagmire's inappropriate comments and his bizarre methods of teaching self-defense. Additionally, the episode features a parody of the classic Western film, "A Fistful of Dollars," which adds to its comedic value. Overall, "A Fistful of Meg" is a funny and entertaining episode that uses humor to address the serious issue of bullying and the importance of self-defense. Quagmire's appearance in the episode adds to its comedic value and makes it a memorable episode for fans of the show.

10 "The Giggity Wife" (S11, Ep11)

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"The Giggity Wife" episode of Family Guy is one of the funniest episodes due to its clever writing and humorous take on the classic TV show, The Bachelor.

The episode revolves around Quagmire's attempt to find a wife and his use of a Bachelor-style reality show to do so. The hilarity ensues as Quagmire attempts to navigate the show's challenges, often with absurd or inappropriate behavior. The episode also features a hilarious subplot involving Brian and Stewie creating their own reality show, which adds to the humor and satire of the episode. Furthermore, there’s also a memorable music number, "Giggity Giggity," which showcases Quagmire's unique catchphrase and adds to the overall comedic tone of the episode. Overall, "The Giggity Wife" is a standout episode due to its clever writing and hilarious take on The Bachelor.

9 "Lottery Fever" (S10, Ep1)

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"Lottery Fever" features the character of Quagmire in a supporting role. The episode centers around the Griffin family, who become obsessed with winning the lottery after discovering they hold the winning ticket. Quagmire appears in the episode as intensely jealous of the Griffin family's newfound wealth. His attempts to get in on the action and cash in on their good fortune.

The episode includes several hilarious moments, such as Peter's outrageous spending spree and Brian's attempt to educate the family on the dangers of money. It’s funny and entertaining episode that uses humor to address the pitfalls of wealth and the importance of staying grounded. Quagmire's appearance in the episode adds to its comedic value and makes it a memorable episode for fans of the show.

8 "Tiegs For Two" (S 9, Ep14)

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In "Tiegs For Two" Quagmire holds a class on how to pick up women, and Peter takes the class in order to improve his relationship with Lois. However, things go awry when Quagmire's teaching methods prove to be unethical and manipulative.

It's a funny episode of Family Guy that satirizes the idea of pick-up artistry and the manipulative tactics often used by men to attract women. The humor in the episode comes from the exaggerated and absurd nature of Quagmire's teaching methods, such as the use of "negging" and "peacocking," as well as the comedic reactions of the male characters as they try to implement these techniques. The humor stems from the irony of Quagmire, who is typically portrayed as a womanizer, being the one to teach the class and then ultimately realizing the harm he has been causing.

7 "Quagmire's Dad" (S8, Ep18)

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"Quagmire's Dad" is a hilarious episode that explores the revelation that Quagmire's father, whom he had always believed to be dead, is actually alive and transitioning to become a woman.

The humor in this episode is derived from the characters' reactions to this news and their interactions with Quagmire's father, now known as Ida. The episode pokes fun at societal norms and expectations surrounding gender, while also highlighting the importance of acceptance and love. The comedic timing of the voice actors, particularly Seth MacFarlane as Quagmire, and the absurdity of the situations presented in the episode add to its hilarity. "Quagmire's Dad" is an excellent example of the show's ability to tackle sensitive subjects with humor and heart, making it a fan-favorite episode.

6 "Big Man on Hippocampus" (S8, Ep10)

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"Big Man on Hippocampus" is a season 8 episode of Family Guy which proves hilarious because it uses a unique storytelling device to explore the character of Peter Griffin's memory loss.

Throughout the episode, Peter undergoes a series of flashbacks and flash-forwards as a result of a head injury, and each scene is presented in a humorous and absurd way. The episode is filled with hilarious sight gags, witty one-liners, and pop culture references. One of the standout moments of the episode is a parody of the opening credits of "The Brady Bunch," featuring Peter and his family members. The episode also includes a running gag involving Peter's constant misremembering of a particular joke, which becomes increasingly ridiculous and absurd as the episode progresses.

5 "Quagmire's Baby" (S8, Ep6)

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"Quagmire's Baby" is a season 8 episode of Family Guy that is known for its humorous take on the topic of parenthood and the responsibilities that come with it. The episode follows the character of Quagmire, who discovers that he has a baby daughter and is forced to adapt to his new role as a father. The episode's humor comes from Quagmire's struggle to balance his wild lifestyle with the demands of fatherhood.

The episode includes several hilarious moments, such as Quagmire's attempts to teach his daughter inappropriate words and his misadventures with a diaper-changing machine. The episode also includes witty one-liners and pop culture references that add to its comedic value. Additionally, the episode features a heartwarming subplot involving Brian, who becomes attached to Quagmire's daughter and develops a strong bond with her. Overall, "Quagmire's Baby" is a funny and entertaining episode that uses humor to address the challenges of parenthood and the importance of family.

4 "Stew-Roids" (S7, Ep13)

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In the "Stew-Roids" episode of Family Guy, Quagmire's relevance comes from his role in helping to expose Stewie's use of steroids to increase his muscle mass and improve his performance in a toddler Olympics competition.

When Stewie becomes addicted to the steroids, Brian and Stewie's coach turn to Quagmire for help in exposing Stewie's drug use. Quagmire helps to gather evidence and comes up with a plan to catch Stewie in the act, which leads to a humorous confrontation between Stewie and his family. One of the funniest moments in the episode is when Quagmire disguises himself as a baby and joins the toddler Olympics competition in order to catch Stewie using steroids. Another humorous moment is when Quagmire uses his knowledge of steroid use to impress a group of bodybuilders at a gym.

3 "Meet The Quagmires" (S5, Ep18)

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"Meet The Quagmires" is a hilarious episode of the animated television series that follows Peter as he's transported back in time to 1984. However, his actions have consequences, and lead to Quagmire and Lois getting together, instead of Lois and Peter.

The humor in this episode comes from the unexpected twist and the absurdity of the situation. It's also amusing to see how different Quagmire's relationship with Lois is compared to Peter's, as Quagmire's womanizing tendencies and lack of emotional depth are at odds with Lois' more serious and grounded personality. Overall, "Meet The Quagmires" is a funny episode due to its combination of cultural references, absurd situations, and unexpected twists. The humor of Quagmire marrying Lois adds an extra layer of hilarity to an already entertaining episode.

Related: The Best Family Guy Episodes and Why They Left an Impact

2 "I Take Thee Quagmire" (S4, Ep21)

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In the episode "I Take Thee Quagmire," Quagmire gets married to a woman named Joan. However, on their honeymoon, Quagmire realizes that he's not ready for marriage and tries to get out of it. When he returns to Quahog, he tries to avoid his wife, but she tracks him down and tries to win him back.

Meanwhile, Peter and the guys discover a new drink that makes them act like idiots. They drink it all night and end up causing chaos in the town. When Quagmire's wife sees them acting so foolishly, she realizes that she doesn't want to be married to Quagmire after all. At the end of the episode, then he discovers that his ex-wife has taken up with his elderly father. The episode ends with Quagmire yelling "Dad, what the hell?!" while his father happily replies "Giggity giggity!"

1 "The Cleveland-Loretta Quagmire" (S4, Ep5)

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In "The Cleveland-Loretta Quagmire", Quagmire's humor mainly comes from his outrageous and over-the-top reactions to the events happening around him. The episode revolves around the revelation that Quagmire's best friend Cleveland's wife Loretta is having an affair with Quagmire. The situation becomes more complicated when Cleveland catches them in the act and decides to leave Loretta.

Quagmire's funny moments in this episode include his ridiculous attempts to deflect blame, his exaggerated facial expressions, and his inappropriate one-liners. He also engages in some physical comedy, such as when he gets stuck in Cleveland's bathtub and has to be rescued by Peter and Joe. Overall, Quagmire's humor in this episode comes from his ability to take a terrible situation and make it even worse with his outrageous behavior and misguided attempts at humor.