15 Saddest How I Met Your Mother Episodes

As tragic and wrenching as Marshall's reactions to his father's death are, both Bad News and Last Words are toned down in the sad department by a solid measure of humour. Season nine's How Your Mother Met Me, though, has no such cushion, and is almost pure drama.

With the episode, audiences finally get an insight into Tracy's backstory, showing her always one step away from Ted throughout the major moments of the show. Not only that, but her boyfriend Max passes away, she loses two roommates, struggles to get back into the dating scene, and wonders whether she can yes to her latest boyfriend's marriage proposal.

All of this is topped-off by her rejecting her boyfriend, unable to let Max go, and singing Le Vie en Rose and playing the ukulele Max bought her before his death. As she sings, Ted listens on, and laments that it was the first time he had ever heard her sing.

The whole episode is a masterpiece, featuring brilliant callbacks to the rest of the show and making Tracy's story just as tragic and messy as Ted's. The emotion is dialled up to eleven, and it's a fantastic if emotionally draining watch.