Sad Times Montage

A sequence in which it is shown that, while time is passing, the protagonist is feeling sad and alone. Opposite of the Good Times Montage. In fact, some films will juxtapose a Sad Times Montage with a Good Times Montage earlier in the film. Can overlap with the Lost Love Montage, with both sides of the lost love being sad, separately. Especially if there's an overlap with the Lost Love Montage, a Cradle of Loneliness may be part of it.

See also Happier Home Movie, which the protagonist may watch in lieu of this.

Anime

 * Makoto Shinkai will make you cry over a montage.

Film

 * The characters in Shortbus have a sad fucking montage.
 * Shrek has one of these right before the big Climax. It's set to the Rufus Wainwright cover of "Hallelujah."
 * In fact, Sad Times Montages set to various covers of "Hallelujah" are practically a sub-trope all their own. Other examples include:
 * The OC (the Jeff Buckley version)
 * The West Wing
 * ER
 * And Scrubs.
 * Music and Lyrics has one.
 * The entire scene of "Without You" from the movie version of Rent
 * Up. The first minutes are two people getting together and marrying. Then there's one thing after another...

Live Action TV

 * Usually happened on Buffy the Vampire Slayer when things when wrong in the lives of the main character and her friends -- which was often.
 * Neatly played with in one episode, however, when Spike has been around after breaking up with Drusilla and basically ends up causing trouble for everyone, which ends up spoiling a lot of different things for different people. By the end of the episode, we see a montage of all the characters looking angsty and wistful... and then we see Spike, who has solved his problem and is currently driving away as happy as Larry, bopping to the Sex Pistols' cover of "My Way".
 * Variant: Another episode had three different women hurt and disappointed by their respective partners, and ended with a shot of all three walking around different sides of the same campus park, but without taking notice of each other - so, actually a bad times non-montage.
 * The end of pretty much every episode of Allie Mc Beal.
 * Misfits brings out one of these close to end of its very first episode, with all five of the main characters trying to recover following the events of the day: Nathan gloomily watches his mother and her boyfriend enjoying themselves; Alisha resigns herself to an evening alone thanks to her newfound power; Kelly lapses into depression over being dumped by her boyfriend- not long after finding out what he really thought of her; Curtis watches old footage of his past athletic triumphs, evidently trying to use his time-travelling powers to undo his mistake; Simon at first appears to be enjoying himself, given that he's standing in the middle of a cluster of friends and smiling... and then it's revealed that he's made himself invisible and is standing in between groups of people in a desperate attempt to assuage his own loneliness. A good look at his face a moment later shows that it isn't working.
 * Played for laughs in The IT Crowd when the shirtless Roy gets locked out of the office building. Lacking his wallet and keys, he turns into a homeless derelict, begging for enough change to make a phone call until Jen finds him again. All of this happens in two hours time.

Web Comics

 * This page and the next one from Everyday Heroes, showing how Jane felt.
 * Gunnerkrigg Court. Kat and Alistair part without a proper goodbye. As a result, on this page, Kat gets progressively more sad, until Annie decides to intervene.

Western Animation

 * The Simpsons uses this frequently.
 * Mocked in Family Guy when Peter has one of these after getting into an accident and having to use a wheelchair - it's revealed that the montage was only a few minutes.
 * In An American Tail where Fievel is walking around in New York alone, searching for his family.
 * In The Venture Bros., after, the first episode of Season 2 opens with a montage of characters looking depressed, Doc breaking down, fleeing the compound in the X-1, and Brock tracking him through various exotic locales as Doc "finds himself". Unusually for most montages of this type, the accompanying music is an upbeat techno track, which undergoes a Diegetic Switch as Brock finally catches Doc at a rave.
 * Futurama. The ending to Jurassic Bark. You know the one. Poor, poor Seymour.