7. The Kelly Song Cheers (S7E19)
No points for ingenuity, musical prowess or big budget productions, but you have to admit that this is probably the sweetest song on this list? These days we can find Woody Harrelson in the more cynical and richly experienced roles, whether that's sporting a shotgun and a Stetson in Zombieland or downing drink after drink as Haymitch in the Hunger Games series, so you'd be forgiven for forgotting how he made a name for himself as the naïve and instantly loveable Woody Boyd on Cheers. Harrelson joined the Cheers cast in their fourth season and racked up an impressive 200 episodes during the series run, as well as guest starring on Frasier. In the episode in question, Woody is dating the rich but equally simple Kelly Gaines. Her father has invited Woody to her birthday party in the hope of embarrassing him and leading Kelly to break up with him when he is not able to afford the kind of gift Kelly is used to (Lamborghinis etc.) After taking Frasier's advice, Woody decides to give her a gift from the heart and instead writes Kelly a song about how much she means to him which he performs at her birthday party in front of all the guests. What results is both a highly comedic and endearing composition that encompasses everything that's characteristic of Woody. And of course, he eventually wins her round and makes her realise there are more important things in life than money, like someone sharing the words 'I love you' for the first time. And given that the couple end up marrying and starting a family, this musical moment gives the episode considerable significance in the context of the series. Like Woody, the song is awkwardly put together but has a heart-warming humility that makes us root for him every time.