33. I Want to Hold Your Hand
(Grilled Cheesus, Season Two) During one of the very earliest episodes of Season Two, the glee club discuss the existence of God and their various religious beliefs. However, Kurt proves the most skeptical to spirituality a view which is fuelled when his father, Burt, collapses with a heart attack and falls into a coma. His take on The Beatles' soft-rock number, which he sings as a plea to his father, is both haunting and heartbreaking. As well as showcasing Chris Colfer's amazing voice, the performance gives us vital background information into Kurts past, his difficult relationship with his father and his untimely mothers death. A sombre moment of clarity amongst the haze of Glee's loveable ridiculousness.
32. Lucky
(Duets, Season Two) A thoroughly charming and chemistry-filled choir room performance, Sam and Quinn's take on Jason Mraz's Lucky is one of those rare occasions when Glee outdoes the original song. New football quarterback Sam is paired with reinstated head-cheerleader, Quinn, who is determined to be reclaim her top dog status. However, its more satisfying to see this almost instant melt away when she meets this new guy, who comes across as mature, kind and genuine and might actually be a good influence on a troubled Quinn. Only this time Quinn and the quarterback have a believable chemistry between them. Chord's voice also compliments Diana's voice much more than Cory's does. Note later in Season Two (in Rumours) during his 'I Don't Want to Know' duet with Dianna, her voice is almost completely drowned out by Cory's.
31. (I've Had) The Time of My Life
(Special Education, Season Two) Continuing on with their budding romance, Sam and Quinn are chosen to open Sectionals, after winning the duets competition with 'Lucky'. They go with the timeless, Dirty Dancing classic and, as expected, kill it! Blonde Ambition! They both have sweet, silky voices which synthesise together flawlessly. It was also a nice change to see a different romance blossoming on the big stage (other than Finchel) and proved that Quinn, despite having a softer voice, can indeed command an audience as well as the other glee girls. Unfortunately, for Quam shippers, it's was also kind of the couple's swan song as the writers, as they are often prone to do, messed up their relationship from hereon in and it never really recovered, or was rarely acknowledged.
30. Landslide
(Sexy, Season Two) Santana's rendition of the Fleetwood Mac favourite is essentially her coming out song (without her actually coming out) and is the first time we really see another facet to the usually cruel and calculating cheerleader. Naya Rivera has a stunning voice, which we were only really being introduced to at this point. Here, she is also aided by guest star Gwyneth Paltrow, who is a much better vocalist than most would have expected. In addition, the performance it is even more memorable because Santana makes herself vulnerable to Brittany, by admitting her love for her, only to be rejected by Brittany, who is still dating Artie. Her experience of rejection is a harsh, but honest, lesson learned by Santana.
29. Blackbird
(Original Song, Season Two) Another Kurt classic from the Season Two Regionals episode. Having been bullied so bad he had to transfer to the private school, Dalton Academy, the home of the New Directions' competitors, The Warblers, Kurt is entrusted with their pure-bred canary bird, Pavarotti. However, when the bird dies suddenly, Kurt dedicates the song to him (another Beatles melody) However, the performance marked a much bigger moment in Glee than Pavarotti's death. It is Blaine's 'realisation moment'. As he says the moment when you realise 'oh, there you are!' This was considerably later in the season and Blaine had finally realised that he liked Kurt in the same way Kurt liked him. Thus, we had the official start of Klaine! The performance also earned Kurt a duet for Regionals, with Blaine.