My first thought is to get a better radio, a Cobra 19 is not much of a performer. Next up a Wilson 1000 might help as well.
If you do try a small amp a KL203 or 200P would be a nice choice. You WILL have to have a shop lower your dead key to 1.5 watts though.
You might check e-bay for a used Uniden 122xl, that would be a much better radio then the Cobra 19 and it has
SSB. You will get double or triple your range on
SSB compared to what your getting now.
To all the naysayers a Lil Wil can work with up to 200 peak watts. Obviously a K-40 or Wilson 1000 would be better.