|Debt It Be|
|Season 1, Episode 20|
|Air Date||December 1, 2006|
|Guest cast|| Peter North|
|Previous|| Money for Nothing,|
Guilt for Free
|Next|| My Boyfriend's Jackson and There's Gonna Be Trouble|
"Debt It Be" is the twentieth episode of the first season. The title is a reference to The Beatles song "Let It Be."
Robby gives Miley and Jackson their own credit cards to only use in emergencies. Miley then goes to the One Day Flea Market but finds that she does not have enough money with her to buy things that she wants. Although initially reluctant to use her credit card, after her pants split she decides that the situation qualifies as an emergency and she needs to buy a skirt; this leads to her caving in completely and buying a large amount of expensive things. When she comes home and talks to Jackson, she realizes how much trouble she is going to be in with her father and decides to return the purchases and get the money back, but by this time the flea market is gone.
She then asks Jackson, who is Marlon Brando in The Godfather and who she refers to as "Godbrother," to help her pay the debt. Jackson hatches a plan to auction off Hannah's old clothes and a fake pair of sapphire earrings given to her for a video. The siblings manage to raise the money to cover her debt and she thinks that they are home free. That is until Robbie tells them that the jeweler wants the sapphire earrings she had worn in a music video shoot back, because they mistakenly gave Hannah the real pair instead of the fake ones. Once she hears that, Miley attempts to gets the earrings back, and finds out that Katherine McCord (the woman who bought them) is living at a senior citizen retirement center.
Miley (dressed as Hannah) and Jackson try to persuade Katherine to sell back the earrings, but she is very attached to them; she does, however, agree to give them up once Miley tells her (falsely) that the earrings had belonged to her grandmother, but will only return them if Miley's grandmother appears in person to claim them. For this purpose, Jackson dresses up as an old lady, Nana Montana, to trick her into giving back the earrings. Unfortunately he messes this up by forgetting to put on any clothes beneath his waist. He and Katherine have a very extended conversation in which she keeps pressing him for more stories from the past; Jackson makes up absurd stories involving President Lincoln, Samuel Morse, and King Kong, while Miley periodically tries, without success, to end the conversation and get the earrings back. In the end it turns out that Robby has found out what is going on and is at the retirement center dressed up as an old man; he had intended to teach his children a lesson and the old woman had been in on his plan.
- When Robby Ray punishes Miley by telling her that she has to clean the garage, Miley says, "But, Daddy, there's spiders in the garage!" In real life, Miley's worst fear is spiders. She revealed this in the Hannah Montana 2-Disc Special Edition Soundtrack.
- Nana Montana is mentioned in the Sonny with a Chance episode "Random Acts of Disrespect".