'25th Hour' (2002)
We first see Lindsey puffing on a cigarette sat on a swing chatting away to Naturelle, played by the beautiful Rosario Dawson. Their talk is naturally geared towards boys and relationships, them being 17/18 year olds, of course. So if you dont fancy tuning in for the highly gorgeous talk of Lindsey trying to set Naturelle up with her brother, Peter, definitely take a look for the Catholic schoolgirl outfit! Yes, you heard me right!
If that's not enough, we have the Puerto Rican-esque accent [rvialled for cuteness with the Texan from Man Of The House] which, albeit a small change [you can still detect the Brooklyn] it's so different to what we usually hear from Vanessa.
The film itself is quite good but highly emotional, with the context surrounding 9/11.