If you know what the basic structure of the items will be, then it's easy.
If you don't know the structure of your items a priori, one approach is to score the items according to their similarity against each other. Using info from this question for the standard library module difflib,
import difflib
import itertools
list_1=['taska1', 'taska2', 'taska3', 'taskb2', 'taska7']
# Initialize a dict, keyed on the items, with 0.0 score to start
score = dict.fromkeys(list_1, 0.0)
# Arrange the items in pairs with each other
for w1, w2 in itertools.combinations(list_1, 2):
# Performs the matching function - see difflib docs
seq=difflib.SequenceMatcher(a=w1, b=w2)
# increment the "match" score for each
score[w1]+=seq.ratio()
score[w2]+=seq.ratio()
# Print the results
>>> score
{'taska1': 3.166666666666667,
'taska2': 3.3333333333333335,
'taska3': 3.166666666666667,
'taska7': 3.1666666666666665,
'taskb2': 2.833333333333333}
It turns out that taskb2 has the lowest score!