First-time feature director Jake Paltrow explores the line between dreams and reality in The Good Night, which had its premiere at the 2007 Sundance Film Festival. Gary Sheller (Martin Freeman), a British ex-pop star living in New York City, is stuck in a stagnant relationship with his long-term girlfriend, Dora (Gwyneth Paltrow). Gary's relationship with Dora is adrift in a sea of ambivalence, and he feels Dora doesn't support him emotionally . Gary and Dora live in the same apartment, share the same bed, but there might as well be an ocean between them; the bridge of communication seems to have long since shut down. Meanwhile, Gary's best friend and former bandmate Paul (Simon Pegg) works for an ad agency and has become Gary's boss, while Gary is relegated to writing jingles that "sound like 'Cheers'."
Then one night, Gary dreams of Anna (Penélope Cruz), a strikingly beautiful woman who exists for the sole purpose of telling Gary how wonderful he is, encouraging him in his music, and fulfilling his sexual fantasies. The trouble is, Gary finds himself more and more not wanting to leave the dream state where he can be with Anna. She makes him feel better about himself, and he finds that he wants to be with her all the time. He seeks out lucid dreaming "expert" Mel (Danny DeVito), who teaches Gary how to enter his dream world any time he wants. But how can Gary ever hope to save his relationship with Dora if he lives more and more in his dreams?