Richard "Ricky" Underwood is one of the main characters and was known for being a bad boy and womanizer in the Grant High School. The abuse he suffered through as a child is responsible for most of his actions. He uses this abuse as an excuse most of the time, to gain sympathy from others. He is the biological child of Bob and Nora Underwood, the adoptive son of Sanjay and Margaret Shakur, and father of John Juergens He was also the husband of Amy Juergens, (he married Amy a couple of years after the series finale events, confirmed by Brenda Hampton). He is portrayed by Daren Kagasoff.
Ricky is the son of Nora and Bob Underwood. Both of his parents were drug addicts and in prison. Ricky got his father sent to prison school for sexually and physically abusing him. He was told by Bob that that he needed to be taught a little lesson about how hard it is to be a man in this world, as an excuse to sexually abuse him. Ricky blamed his mother for not stopping Bob when he was younger.
Ricky went to school and told everything to his teachers about his abuse. After that, he was put into foster care and his foster parents got him into therapy. After being in several different foster homes he ended up in a stable home (Margaret and Sanjay Shakur). The abuse had a profound affect on Ricky's life. Consequently, he slept around a lot because he realized he could use his looks to manipulate women and naive girls into sleeping with him. He usually did this by saying "I love you", but never really meaning it.
Ricky had a one night stand with Amy Juergens at band camp. He found out about her pregnancy by hearing the rumors around school. At first he didn't want anything to do with Amy or the baby, and she had definite misgivings about going through with the pregnancy. He even denies the baby is his when Amy is at the abortion clinic. He pretends to Grace Bowman that he is concerned about Amy, but he is just acting so he can manipulate Grace into sleeping with him. All he really wanted was to sleep with Adrian Lee and continue his life like usual. He went to Adrian's apartment after having a small argument with his foster parents. He refused to go to school, but she went ahead because she had to turn in her English Lit paper but allowed him to stay. Ricky tries persuade her to stay and she reluctantly agrees to return after her English Lit class. Unexpectedly, Amy's father George Juergens stops by Adrian's house, recognizes Ricky, and has a conversation with him. He states that Ricky will have nothing to do with the baby when it comes, or even see the baby. George tells him that there is one thing that he is sure about - Ricky will be paying child support for the baby until he or she turns eighteen.
Ricky was offended by what Mr. Juergens said, and went to his therapist to talk about it. The therapy got Ricky thinking that he doesn't want to become like his father, who doesn't care for him. After the session. he went to Amy's house and told her that he would like to talk to her and her parents about what's best for the baby, and states that he wants to be involved. He does want to see his baby and take care of him or her. Ricky later decides that he wants to have a more serious relationship with Adrian and tells her he doesn't want her sleeping with other guys, he on the other hand wants to sleep with other girls while still being in a relationship with Adrian. Adrian threatens Ricky not to sleep with anyone, but he cheats on her anyway with Zoe. She later tells him not to touch Amy, but he again lies, and kisses Amy, by claiming they were practice kissing. It is shown that Ricky does what ever it takes to gain approval from people which influences the fans that he is a good person. However it is shown to other fans that his character lacks any compassion for others save for those who can do for him.
This causes Adrian to become furious, and she gets back at both Ricky and Amy by sleeping with Ben. Both Adrian and Ben thought that Ricky and Amy had done much more than kissing. Meanwhile, Ricky is also dealing with the fact that Ashley has a crush on him and that he has a slight attraction to her in return. The attraction escalates until Ricky and Ashley kiss, but Ricky ends the kiss. During this time Ricky decides he doesn't have feelings for Amy, and tries to get Ben and Amy back together. He goes to Ben's home while Leo is on his honeymoon with Betty and convinces both Amy and Ben to give their relationship another chance.
When Ricky finds out Adrian is pregnant with Ben's baby he decides to start a relationship with Amy for unknown reasons. Ricky and Amy finally get the chance to start thinking about what they want their relationship to be in the episode Up All Night while in New York. Amy returns home early because she starts to question whether Ricky can maintain an exclusive relationship. Amy convinces Ricky to date her, stating that that is how it usually happens that people go on dates and fall in love. Ricky is unsure about the idea, but goes along with the plan. It the episode Who Do You Trust Ricky is tested for STD's after Amy states that she is ready to have sex, but only after she sees his test results. Ricky and Amy continue to date, and Amy and John move into the apartment in the episode "When One Door Closes".
Ricky and Amy continue to have relationship issues that they seem to fester over time. Amy then tries to persuade Ricky to propose to her but he does not want to get married at the moment. But at graduation, Ricky is named Valedictorian, but he won't admit he doesn't deserve to be because he cheated most of high school and he proposes to Amy during his speech. Amy is hesitant to set a date, and states she just wanted the ring, Ricky then tells Amy he does want to get married and didn't give her the ring to mark his territory.
Ricky and Amy continue to have relationship problems when she decides she wants to go to summer school. She finally decides a date 4th of July, but rumors start to fly about her that apparently she is gay, just because her mother is. Amy decides she can't deal with it anymore so her and Ricky decide to elope. This is evident in his relationship with Grace, and Adrian that he is not supportive of their needs. also in his friendships with both Ben and Ashley
However Ricky chooses a crazy minister who claims his name is Dicky and dances with a possum so he runs out. They lie about the marriage and accept gifts of antique rings from his parents, a song and dance from school, and money and insurance. Later George and Ben it's discover that Amy and Ricky aren't actually married and are just pretending to be. Ricky then gets fed up of pretending and tells her he wants to properly get married.
However when Ricky meets an old friend Clementine from his days as an orphan he begins to develop a relationship with her. This relationship appears to be platonic at first, but later Ricky begins to meet with Clementine in secret without Amy. He also begins to walk her back to her dorm room claiming to want to protect her from a pimp who later attacks Jack. Ricky's views toward marriage later change when he meets Clementine, which then spurs Amy to want to get legally married, but Ricky is still reluctant to go through with it. He later attempts to intimidate Ben in the hospital while Jack is being treated, about keeping he and Amy being fake married a secret. It is later revealed when talking with his foster brother Ethan about sex, that Ricky doesn't like having sex with Amy.
Amy breaks off their engagement and moves to New York to go to university in the series finale. Amy realized that Ben was not the one for her and that Ricky was while she was in Hudson University and got married. (Revealed by Brenda Hampton).
- Start: 6 weeks before pilot
- End: 6 weeks before pilot
- Reason: It was just a one-night stand.
- This is seen in a flashback: One Night at Band Camp
- Reason: It was just a one-night stand.
- Start: Rules of Engagement (3x14)
- Engagement: And Circumstance (4x13)
- End: Thank You and Goodbye (5x24)
- Reason: They were not in love.
- Start: 2 years after 5x24 (series finale)
- Engagement: Unknown
- Marriage: 2015 - present
- Reason: Amy realized that Ben was not the one for her and that Ricky was while she was in Hudson University (Revealed by Brenda Hampton).
- Start: I Feel Sick (1x03)
- End: Chocolate Cake (1x16)
- Reason: Grace finds out that Ricky is still sleeping with Adrian. Grace is also scared of Ricky's dad.
- He would have sex with girls and then try to completely avoid them afterward. The only girls he was shown to try and hook up with again having sex were Amy and Adrian. Shawn is also implied to have had sex with him and he did try to hook up with her again, but it was never explicitly confirmed that they had sex.
- It is shown in the first episode Ricky pays Joe Hampton to do some of his assignments for him. With this information it can be determined that Ricky did not deserve the "Governor's Award" or to be "Valedictorian".
- He tells every girl that he sleeps with that "He loves them".
- He lives with his fiance and his son in his apartment above the butcher shop.
- His father abused him when he was young, and uses that incident to explain why he has indiscriminate sex with several women.
- He works with Ben in the butcher shop.
- Ricky seems to be one of the weaker emotionally based male characters on the show despite the hardcore exterior he tries to project to others. This makes him to be more sensitive because he cries a lot during the series.
- In Season 2 of the show he began to flirt with Ashley bunny. Although she is John's aunt he claims that they were only friends, and stops returning her advances in the beginning of Season 3. He claims that he wants to start a relationship with Amy so she can love him, and later avoids Ashley completely.
- He has never really been able to support anyone emotionally save for Amy, and Grace. Totally abandons both Adrian and Ben after the death of their child.
- He claims that he is friends with Ben Boykewich, but it is shown that their friendship is really a rivalry in which Ricky continues to show Ben he is better than him at everything. He makes a statement to Ben in Season 1 claiming that "He would have his father, Amy, and the baby on his side before he could say pork chop".
- This rivalry has gone on from not only Amy and Adrian, but also to he could have the better relationship, and the better kid. It also extended to Ben's father, and Boykewich company in General. However Ben has made it clear he does not want to run his father's company.
- In the Season 4 episode "And Circumstance", it is revealed that Ricky had a 4.2 GPA average and highest SAT scores of the graduating class.
- In the Season 5 mid season finale "Half Over", Ricky tries to intimidate Ben in the hospital about not revealing the secret about he and Amy. He tells Ben that Amy have John, Ben does not have a chance. This statement presumably has a strange effect on Ben who admits he is right.
- Margaret Shakur said she stop receiving money from the state when she adopted him.