The Seagull

"I am unhappy."

—The third sentence of The Seagull.

Konstantin, the only child of the acclaimed actress Arkadina, has written a play that will in one stroke repudiate the stodgy realism of his mother's work, announce his literary arrival, and, after a childhood of obscurity, win the respect of his family and neighbors. Unfortunately, his mother, who thinks little of her son and resents Nina, the pretty young star of the show, ruins the grand premiere with heckling.

Titanically angry at Arkadina and immensely jealous of her lover Trigorin, a famous writer, Konstantin shoots a seagull and presents it to Nina as a cryptic omen of his despair, which succeeds only in driving her into Trigorin's arms. Konstantin then shoots himself in the head.

He gets better. Things get worse...

The Seagull, the first and perhaps most famous of Anton Chekhov's major plays, was itself a horrendous failure at its first performance. Its very delicate treatment of human weakness can easily become leaden and somber if handled the wrong way, but good production and acting illuminates its immense insight and compassion, and can even pull some laughs from odd places.

Tropes used in The Seagull include:

Artist Disillusionment
As You Know: Partially invoked with Konstantin telling Dorn the story of Nina and Trigorin's affair in Act IV--Dorn knows half of it already, but Konstantin says it anyway.
Attention Whore: Arkadina.
Black Comedy: Chekhov actually labeled the play a comedy, and it does contain quite a few pratfalls and deadpan snarks (Konstantin's play is hilarious). Whether the blackness of the drama or the comedy of the characters' neuroses predominates in any given production is a matter of directorial choice. Most modern directors naturally go with the former.
Break the Cutie: Nina.
Chekhov's Gun: Though written by the Trope Maker, the question of whether this play utilizes it is up for debate.
Diabolus Ex Machina: One interpretation of the climactic scene of Act IV. Konstantin has finally achieved success as a writer and though he is glum and lifeless, he seems to have reached an emotional equilibrium. Perhaps part of him even has hope for the future. Then Nina returns, and even after everything that's happened, she still loves Trigorin, thus destroying Konstantin's last bit of hope and leaving him ready to kill himself.
Downer Ending: And how.
Driven to Suicide: Konstantin tries to kill himself at the end of Act II, but fails. He succeeds in Act IV.
Dysfunction Junction: Pretty much every character is solipsistic, cruel, cowardly, depressive, or all four at once.
Generation Xerox: Like her mother, Masha is doomed to marry a man she despises, and before Konstantin succeeds at his second suicide attempt, he seems set to become a wasted never-was like his uncle.
Girl Next Door: Nina.
The Ingenue: Nina.
Large Ham: Arkadina, who's unwilling and/or unable to turn off the Great Actress persona when she's at home.
Like Father, Like Son: In one translation (the best one this troper has read), Irina says this to Konstantin straight up: (referring to him) "People with no talent always try and belittle the ones with real talent! Just like your father!"
Love Dodecahedron: Medviedenko loves Masha, Masha loves Konstantin, Konstantin loves Nina, Nina loves Trigorin, Irina also loves Trigorin, Trigorin loves them both (sorta), and Konstantin loves Irina (though in what way depends upon your opinions about Freud). Meanwhile, Polina is married to Shamraev but loved/loves Dorn, and he's a difficult one to peg.
Luke, I Am Your Father: Averted. Chekhov all but states that Dr. Dorn is Masha's father, but no explicit revelation ever comes.
Parental Abandonment: Mr. Trepliev up and leaves right off, and through most of the rest of Konstantin's life his mother is a distant (if influential) figure.
Show Within a Show: Konstantin's play.
Stylistic Suck: Konstantin's play. Again.
Time Skip: Two years between Act III and Act IV.
Unlucky Childhood Friend: Masha.