YMMV / Rampage of the Rail Bandits

• Hilarious in Hindsight: During the song Rosie's Blues, Rosie imagines herself painted blue like Thomas. Come the next year in Season 21, she has been repainted a new livery (albeit not one that resembles Thomas even remotely).
• Iron Woobie: Rosie begins the story by wrecking a bridge on Thomas' branch line, causing said line to close to fix the bridge and earning Thomas' displeasure. Then she ends up getting involved in stopping the Rail Bandits and faces moments where she could have been derailed or died. Nevertheless, she still bravely soldiers on to achieve her happy ending.
• Jerkass Woobie: Jeb may be one of the villains, but owing to his abuse at Slim Jim's hands, it's hard not to feel a little bit of pity for him.
• The Woobie: Rosie especially, although Oliver and Samson have it pretty rough too.