fruit = ['banana', 'melon', 'lime', 'somereallylongfruit', 'kiwi'] print [i for i in fruit if len(i) == max([len(j) for j in fruit])][0] somereallylongfruit print [len(j) for j in fruit] [6, 5, 4, 19, 4] fruit = ['a', 'melon', 'kiwis', 'grape', 'lime'] print [i for i in fruit if len(i) == max([len(j) for j in fruit])][0] melon