You could use a list comprehension to add the elements from both lists zipped together, and use itertools.cycle so that the iterator a repeats itself as many times as necessary until b is exhausted:
from itertools import cycle
a = [50, 17, 54, 26]
b = [19,  7,  8, 18, 36, 8, 18, 36, 18, 14]
[i+j for i,j in zip(cycle(a), b)]
 Output  
[69, 24, 62, 44, 86, 25, 72, 62, 68, 31]
 Details 
If you take a look at the iterator of tuples generated from the zipped expression:
list(zip(cycle(a),b))
[(50, 19),
 (17, 7),
 (54, 8),
 (26, 18),
 (50, 36),
 (17, 8),
 (54, 18),
 (26, 36),
 (50, 18),
 (17, 14)]
You can see that the elements in a cycle around until the other iterator is exhausted, making it very easy to perform some operation on the interleaved elements.