<b>Python 2.7 <s>334</s> <s>335</s> <s>327</s> 314 Characters</b> (My first time golfing) (335) Forgot to escape newline. (327) Removed redundant 100 for randint. Comparison of first character of response, instead of whole string. (314) Updated printing who won. from random import* i=input s="Enter number:" p=i("Player 1/2:")-1 h=100 exec("N=i(s)","N=randint(1,h)")[p] b=l=0 for _ in[0]*5: exec("g=(h+l)/2;r=raw_input('Guessing '+`g`+':');exec(('h=g','l=g')[r[0]=='l'],'b=1')[r[0]=='c']","g=i(s);b=g==N;print(('higher','lower')[N<g],'correct')[b]")[p] if b:break print 1+b,"won"