"You're unlovable Richard. Pearl only loved you because your parents paid her to."
—Madalena, "Joust Friends"
As a child Madalena led an impoverished upbringing; her only friend at the time was a beloved pet goat she had named Jenny. She learned at a young age the harshness of life when at one point her parents couldn't afford food. Madalena was then forced to slaughter and eat Jenny. This incident hardened Madalena and made her never want to be put in that kind of position again. Another incident occurred during her childhood years that began to shape her view of the world. One day she was out walking when a carriage drove through the path. Inside, two beautiful princesses sat laughing. The young Madalena immediately found a liking to their earrings. The two girls happened to be the Basikobitcz sisters, Ivanna and Catherine. They called her over and invited her to ride in their carriage but as soon as Madalena stepped up to get in, they had the driver pull away. Cackling they again invited her in but pulled the same trick on her. As they drove away they began laughing really hard saying: "You're so poor". This drove Madalena into wanting to be just like them.
When she became an adult she began seeing the hero known as Galavant. Although their relationship was mostly physical, Galavant truly loved her. One day, when Galavant was buying her a token of affection, Madalena was approached by King Richard who tried and failed to woo her. Undeterred, Richard had his henchman Gareth kidnap Madalena and take her back to his castle. A wedding ceremony was promptly organized with Madalena forced to be the Kings bride. Galavant stormed the castle and crashed the wedding intent on rescuing his beloved. However, Madalena decided to go through with the marriage to King Richard because of the fame, fortune and power he had to offer her. She quickly embraced her new lavish lifestyle while also denying the King intimacy by claiming she took a vow of chastity. She ended up cheating on Richard by taking the court Jester as a lover.
One miserable year later, Madalena has changed drastically from the beloved maiden Galavant once loved. She's become spiteful, sarcastic, uncaring, and cold. She hates her marriage and the king, using Galavant as a means to manipulate King Richard's plans, such as steal the priceless Jewel of Valencia. Although Richard does find the jewel he does not tell her and uses it as a way to lure Galavant along with Isabella.(Pilot)
At dinner one night with King Richard, Madalena shows her hatred towards his acts, such as not feeding himself and leaves in disgust. The next day they return to dinner and Richard appears to act differently, despite these changes Madalena still shares her hatred of him, saying he is unlovable, but not before sharing a story of how she had to skin, cook and eat her pet goat Jenny when she was a girl, due to her family running out of money and food. They then sing 'Maybe You're Not the Worst Thing Ever'. (Joust Friends)
Almost the entire kingdom knows of the open affairs she has, one of which was with the court jester. But the King was completely oblivious to it, until it was accidentally spoken aloud to him. Richard is oblivious that, she cares nothing for him and believes she started her affair with the jester because of his sense of humor.(Two Balls)
Desperate to win her, he begs the jester to coach him how to make her laugh. Though he succeeds through an old cliche, it doesn't change anything for her with him. Its afterwards we see that Madalena has a sadistic side.After the skit, Madalena clearly wants to continue her affair behind Richard's back. However, after bonding with him, the Jester begins to feel guilt and denies their regular encounter. Angered that he won't sleep with her, she has the guards put her then former lover in the scariest dungeon as punishment.(Comedy Gold)
Queen Madalena storms into the throne room looking for her handmaiden and finds Gwynne with the Chef who was awkwardky flirting with her. Suspicious of her husband andGareth's behavior, Madalena lashes out at them for not having found the Jewel of Valencia. She goes back to her room and decides that the only one she can count on is herself ("No One But You").Madalena enlists the Chef's help to find out what the King is planning. She bribes him by offering to arrange him a date with Gwynne and the Chef takes her to the location of the King's secret meeting.While hiding in the castles hallway, Madalena learns of the Kings plan and concocts one of her own. Madalena sends out a message via carrier pigeon and tells the Chef to prepare a special dinner ostensibly for his date with her handmaiden.Queen Madalena makes her presence known and warmly greets her confused ex-lover. She tells him they have a lot of catching up to do and mentions a plan she has set in motion. She also hints at a mysterious partner who is coming soon. Madalena tells Galavant that he's someone who's going to help execute her scheme and that his arrival will cause everything to change.(Completely Mad...Alena)
Over the dinner Madelana had prepared, Galavant and her catch up as he relates the trails he went through to reunite with her. He again declares his love for her but she doesn't definitively recipricate his feelings leaving Galavant confused ("I Love You"). Accompanied by Gareth, Madalena takes Galavant back to the dungeons and tells him to wait there until the arrival of her co-conspirator. Afterwards, Richard returns from his journey of self discovery and "breaks up" with Madalena ordering Gareth to escort her to the dungeon forever, however, Kinglsey arrives and agrees to marry her.(Dungeons and Dragon Lady)
Madalena introduces the prisoners to Kingsley, her future husband and brother-in-law. Madalena is 'poisoned' with the food she is allergic too along with the other guests of the feast.When Richard announces that he will fight his own duel. Satisfied, Kingsley says that he will still have Gareth as his champion. Madalena admiringly says that she's really turned on by Kingsley... and then runs back to the bathroom.(My Cousin Izzy)
Once Galavant and Richard are drunk, they sneak into the palace and head for Kingsley's room. They come to Madalena's room and discover a line of men outside, auditioning for the role of the queen's new consort. Richard advises them to check Madalena's feet and they go to the dungeon. At the castle, Richard and Madalena summon Gareth when they learn that Galavant has disappeared. Gareth claims that he overslept, and Madalena tells him to kill the others. Gareth agrees and goes to the dungeon, back at the throne room, Gareth admits that he didn't kill anyone. Kingsley, furious, declares that the kingdom has gone soft and draw's the king's sword from his scabbard. As he advances on Gareth, Madalena stabs Kingsley in the back, killing him. She tells Gareth that Kingsley wasn't her type and gestures to him to take Richard's throne. After a moment, Gareth takes the king's sword and sits down.(It's All in the Executions)
After her perfectly executed coup Madalena rules over Valencia with an iron fist. She presides over all matters regarding the Valencians (some more trivial than others). She becomes quite annoyed with Gareth and his insistence that he become king but ultimately gives in and allows him to don the title (A New Season aka Suck It Cancellation Bear)
Madalena is said to have once been sweet, lovable and kind hearted person who saw the best in Galavant, but since her capture at the hands of King Richard she has become cruel, self centered and spiteful. Doing anything she can to get her way Madalena is cunning and tends to use any items at her disposal, such as King Richard's cruel brother Kingsley, in order to manipulate a situation to her own liking.
Her tendency to thrive in the rich easy going lifestyle has spawned from her childhood in poverty, being starved and having to kill her childhood friend and beloved pet goat in order to have something to eat.