9. Funny People (2009)
Judd Apatow has made various comedy masterclasses, from The 40-Year-Old Virgin (2005), Knocked Up (2007) and This is 40 (2012) , and whilst all of these films push or exceed the two-hour mark, none of the director's movies suffer more due to their length than 2009's Funny People.
Starring the likes of Adam Sandler, Seth Rogen, Leslie Mann and Jonah Hill, Funny People drags for an arduous 146 minutes, far, far longer than it really should have.
Following veteran comedian George Simmons (Sandler) as he learns he has a terminal illness and seeks to fix the relationships in his life, the film has a lot more heart than Apatow's other pictures and has some striking moments of humour and thoughtfulness.
Unfortunately, the film gets bloated as it approaches its second hour, as many of the scenes find themselves dragging because of Apatow's love of cast improvisation. More than anything, Funny People is the kind of comedy flick that could have done with a more thorough edit.
Within the over-long picture, there's a truly great comedy-drama waiting to be seen, but thanks to its length it's never fully realised.