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Amazing, But Not a Feel-Good Musical
Spoilers!

The thing about "Pippin" is that, supposedly, the whole musical has nothing to do with the assumed setting. "Pippin" is more accurately applied to current times and when seen live, this is often communicated through anachronisms in the costumes or set pieces. "Pippin" is about any of us, feeling lost without direction towards what we are supposed to grow to be.

Actually, "Pippin" is often assumed to take place entirely inside Pippin's head. This explains a lot of the surreal events (Charles coming back to life) and general extremities throughout the show. Pippin imagines that his whole life is one long show, full of deception. His family is not actually his family, but actors playing a horrific version of his family full of backstabbing, incest and unachievable standards. The players are not friendly; they are parts of Pippin's mind trying to convince him to commit suicide. The Leading Player lies to Pippin at every turn and helps him fail at everything he tries, in order to bring him closer to the Grand Finale (setting himself on fire). If we accept that "Pippin" is entirely imagined, Pippin is making himself fail at everything.

When Pippin refuses to do the Grand Finale, the players turn to the audience and ask for volunteers to do the Grand Finale in Pippin's place. They say "Why, we're right inside your heads," which I can only interpret as them saying that they live in all of us. They are waiting in the corners of our mind to push us to suicide. This is backed by the constant references that this show has happened before. The players have caused others to do the Grand Finale, to commit suicide. However, Pippin refuses and settles for an ordinary, boring life, instead of being seduced into the Finale and its promises of fame.

"Pippin" is not meant to be take literally. It is meant to be symbolic and disturbing (This is Fosse we are talking about). This musical is a commentary about mental illness and depression in young people.

Read a better analysis at http://www.newlinetheatre.com/pippinchapter.html :)
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The thing about Pippin is...
Here's the thing about Pippin: Its book is so "open to interpretation" (read "confused") and its icon status due to Fosse's choreography and Ben Vereen's legendary performance have left the public with a very strong impression of what Pippin SHOULD be. Honestly, Pippin CAN be just about anything, which is its greatest strength and largest weakness.

On one level, Pippin is simply the story of a teenager trying to find himself, a common enough but always touching plot. On another level, it's an analysis of the raw showmanship and pure spectacle that Broadway has traditionally relied on in its storytelling, and whether or not this is a healthy or fulfilling way to tell a story (SPOILERS: it's not.) On another level, it's a cautionary tale about mental illness, a boy who imagines an entire world for himself in order to feel the least bit valued in life. On yet another level, it's a piece of existential angst about the inevitability of death and whether one should accept and allow it to slowly creep upon you over time, or live wildly and youthfully, going out in a literal blaze of glory.

The thing about Pippin is...it is completely up to the director. If you've got someone who has a clear vision for how to do the show, which aspects to focus on, how to define the look, attitude, and personas of the Players...Pippin can be one of the most amazing musicals an audience will ever see, something which transforms their life (as it happened to be for me.) If you've got someone who doesn't really know what they want to do...it can be a horrendously boring, or worse, a thematically confused and contradictory show.

All of the tools, themes, and concepts are there for the director to use, it's up to them simply to implement them in the best way possible. Obviously a larger budget opens more doors, but I've seen Pippin done on extremely small budgets and be phenomenal. Obviously casting is important, especially for the Leading Player and Pippin, as their dynamic is really what keeps the audience watching. The Leading Player is one of the most physically, emotionally, and mentally demanding roles in musical theater, and it is extremely hard for Pippin to be likable (he basically whines for 3 straight hours.) But when all of the ingredients do come together, Pippin is a truly amazing piece of American musical theater. Again, if it all works.
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Pippin: His Life and Times, or "130 Minutes of Pointless Audience Down Talking" (also known as "Creepy Vareity Show!"
So things actually start off really well with Magic to Do which is a fun yet creepy number. The following monologue is funny too and Pippin is a charming character with a great following song. Then ofncourse, when the whole conflict is set up and Charles is introduced, things get more fun. War is a Science and Glory are both incredibly creepy.

Then the show really plummets. Though a fun number, No Time at All is pointless and as a character, the grandmother is pointless too. With You really stinks because Pippin isn't supposed to mean what he says, but he does. Then suddenly an ORGY! Then Pippin, along his journey hears that Charles is EVIL and wants to kill him! Meanwhile we're treated to a deliciously evil number called "Spread A Little Sunshine" where Fastrada reveals she doesn't even care about Lewis and is using him as a scheme.

Meanwhile, Pippin comes in and talks to his father, dragging out what could have been an interesting scene into a long father/son moment where we feel like Schwartz's political agenda is beating us against the head. So after Charles reveals his true colours, Pippin stabs him then suddenly becomes the king. So he's king and all and blah blah blah, and after witnessing how hard it is to be king, gives up the throne and calls for our Narrator to revive Charles, and ta-da, he's alive!

Pippin gets depressed and our narrator gives a glimmer of hope with a catchy number called "On the Right Track". Which is followed by an emo moment by Pippin, and suddenly a love interest is brought in. Catherine lives with Theo, who has a pet duck. So they're married for a year and all and Pippin is still depressed and Catherine talks to him sweetly, and Narrator shouts at her to be more nagging, which she is!! And then.. Dammit, work is so hard, can't I be ORDINARY!

Oh, and then there's a pointless sex scene and love song. Pippin later reveals he's suddenly leaving. Catherine then sings about how she misses him, though their relationship has as much depth as a soggy paper plate. Then the finale comes, where Narrator tries to get Pippin to kill himself, and he almost does, but realizes that he was in one big long pointless journey, while we scratch our heads. Narrator asks if anyone in the crowd wants to kill themselves. No, we don't.

Then at the end, Theo is next. Ooh I want a sequel!!!

No, actually, I do not.
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