If you're looking for anime similar to Mawaru Penguin Drum, you might like these titles. All recommendations are made by Anime-Planet users like you!
Fujiko Mine: a woman so beguiling that the greatest thief on earth, Lupin III, has vowed to claim her as his most prized quarry. And while men lust after her, she only has eyes for one thing – all the beautiful treasures in the world that she can possibly steal. From the haunted opera houses of Japan to the boobie-trapped pyramids of Egypt, Fujiko uses both violence and sex to manipulate those who stand in her way. But with the tireless Lupin intervening in every situation to 'take' her, and the skilled rogues Jigen and Goemon entangling their own personal vendettas with hers, how is a woman to realize her wildest desires?
Though the beginning bunch of episodes from each of these series have little in common, the last halves (where the actual, meaty plot starts to kick in) are similar. Both are a blend of mystery and in-depth character study, with a heavy dose of allegory/metaphor, and some pretty surreal imagery.
They also both touch on some of the same themes, most of which are spoilers, so you'll just have to trust me on this one.
Area 11 is still under Britannian rule and the Elevens remain brutally oppressed; what’s more, their saviour, Zero, is nowhere to be found and all of Britannia believes the rebellion is finally over. Elsewhere, having lost the battle, Lelouch sets his sights upon winning the war – but the task is no easier since the Britannian forces have learned some valuable lessons all of their own. Not only have they discovered his identity and captured many of his Black Knights, but they now manipulate the memories of all of his friends. Worst of all, they have taken the most precious thing in his life – his dear sister, Nunnally. With his hatred for the Britannians stronger than ever before, Lelouch must now recuperate his forces and bring their rule of terror to an end.
Giovanni is a young cat with a troubled childhood -- he is bullied in school, and waits patiently day after day for his father to return from his journey. One festive evening, Giovanni and his friend Camponella find themselves aboard a great train which takes them to the edge of the universe and back. However, in the midst of the sights and wonders, Giovanni soon begins to discover that the train's purpose might be much different than it appears.
Mawaru Penguindrum was heavily influenced by, and frequently references Night on the Galactic Railroad. If you want to understand all the symbolism, you should read/watch this classic children's story.
Similarly, if you enjoyed NotGR and are interested in a more modern spin on some of the same themes, you should watch Penguindrum.
Once there lived an eccentric author called Drosselmeyer who wrote grand tragedies - one of them was the tale of a prince who sealed away an evil raven by breaking his own heart into tiny pieces. However, before the story could be completed, the author died and the tale took on a life of its own. Now, in a town where fiction and reality meet, the story continues on its tragic course with Ahiru, a duck who transforms into the beautiful Princess Tutu in order to restore the prince's heart. But will Ahiru's act of love be enough to defy the story's terrible destiny and lead to a happy ending?
Both Princess Tutu and Mawaru Penguin Drum are beautiful works of fantasy in which your own imagination plays a part. It's not just about the objective plot of the story, but how you interpret it and the emotional experience you gain from the process. While Penguin Drum takes plenty of short cuts with the animation, I found both shows had equally lovely character designs, stunning atmosphere (owing a lot to the direction), and a quirky approach that charms over and over again. Furthemore, in both, the characters rarely turn out to be as straightforward as they first appeared. If you liked the approach in one show, you'll love the other.
This is a bit of a gut-feeling rec, but Shima's backstory (Kono Danshi) reminded me of the Child Broiler scenes from Penguindrum, and Kanba's story to a lesser extent. Both stories are about normal teenagers who, after a great personal tragedy, find themselves enmeshed in a supernatural drama.