Richard "Ricky" Underwood lll is one of the main characters and was known for being a bad boy and womanizer in the Grant High School, yet he is what he calls “Damaged Inventory.” He is the biological child of Bob and Nora Underwood, the adoptive son of Sanjay and Margaret Shakur, the foster brother of Ethan, and the father of John Juergens. He is also the husband of Amy Juergens (he married Amy a couple of years after the series finale events, confirmed by Brenda). He is portrayed by Daren Kagasoff.
His father, Bob, is a drug addict who beat Ricky's mother Nora and sexually abused Ricky as a young child. His mother was both a drug addict and an alcoholic who never helped him out of fear. Ricky claims this abuse was responsible for most of his future actions. Ricky was taken away from his parents after the abuse came to light, and put into foster care. As a teenager, Ricky attended Ulysses S. Grant High School, where he was the drummer in the high school marching band and had a reputation of being a promiscuous bad boy.
He used to see a therapist, Lauren's father Dr. Ken Fields, who he occasionally visits for advice as an adult. The summer before Ricky's sophomore year, he had a one night stand with Amy Juergens because she was a virgin and bored at band camp. It was short and bad sex, and he didn't use protection of any kind. He also knocked her up. He denies even being the father to others for a large part of her pregnancy even finding out about her pregnancy a few days later. Despite his misgivings over being a good father, Ricky is shown to love and care for his son John. He and Amy go on a date in the fall finale of season 3 and she makes him get tested before considering having sex with him.
Ricky tests disease-free, and chooses to have sex with nobody other than Amy. Their first time having sex since Ricky got Amy pregnant occurred in the wake of dealing with the news of Ben and Adrian's stillborn daughter. Amy and John soon move in with Ricky. Amy finds messages left by Ben, after telling her she's in love with Ricky. Amy gets caught by Ricky, with him stating they should spend some time apart if she can't trust him. Ricky eventually apologizes to Amy and they get back together. Amy tries to get Ricky to propose by doing "wild" things such as giving him a milkshake and a bath. Ricky ends up being convinced, and at the end of his speech, he proposes to Amy. At the graduation party, Amy allows Ricky to kiss Adrian one last time to give them closure.
Ricky wants to know when Amy wants to get married and is taken aback when Amy doesn't seem to be in a hurry to plan their wedding. Amy told everyone that Ricky and her eloped in the season 5 premiere even though they pulled out at the last minute. Eventually, Amy breaks up with him and leaves John in his care while she goes to New York to attend college. Eventually, Ricky and John move to New York to be a family, with Amy. The two would end up falling in love and getting married.
- Start: Prior to Falling in Love (1x01)
- End: Prior to Falling in Love (1x01)
- 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)
- Elope: To Begin With (5x01)
- End: Thank You and Goodbye (5x24)
- Reason: Amy decides that she needed to take a break from her life with Ricky and John to focus on her future and believes that she still might have feelings for Ben. She ends up moving to New York City for college and leaves Ricky and John in California.
- After a couple of years, Ricky and John moved to New York, along with George. Amy and Ricky fell in love with each other, and got married after they both graduated.(he married Amy a couple of years after the series finale events, confirmed by Brenda.
- Start: Before Falling in Love
- Off and on relationship between start and end(mainly sexual)
- End: Good Girls and Boys (2x22)
- Reason: Adrian had sex with Ben.
- After learning Ben and Adrian had sex Ricky is upset and cries, he later left town to visit his mom, Nora.
- When he returned he blamed Adrian for their break up, even though he gave her no respect, honesty, or emotional support as she did for him.
- He also admitted he only used her for sex, and he cheated on her repeatedly.
- 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. Ricky was a lying, two-timing jerk who lied and tried to manipulate her by using her faith. He also lied to her about not being the father of Amy's baby when she asked for his help at the abortion clinic.
- 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 be more sensitive because he cries a lot during the series.
- In Season 2 of the show, he began to flirt with Ashley Juergens, Amy's younger sister. 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 so 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. Ricky wants to run the company, but will most likely drive it into the ground.
- In the Season 4 episode "And Circumstance", it is revealed that Ricky had a 4.2 GPA average and the highest SAT score in 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 him and Amy. He tells Ben that Amy has 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.
- He is currently married to Amy, and the two reside in New York City with John.
- Ricky is working with Leo to create a high-end fast food chain.