Caption This Compilations! 51-100










































#91 Episode 2.08 – “Crossroads Blues” winner – ccarmich52




winner – suenash19







Nate Winchester is an aspiring author, blogger, and strangely the only male writer for The Winchester Family Business.











































#91 Episode 2.08 – “Crossroads Blues” winner – ccarmich52




winner – suenash19







Nate Winchester is an aspiring author, blogger, and strangely the only male writer for The Winchester Family Business.
With Caption This at the 440 mark (!), we thought it might be fun to cover the previous winners, 50 at a time. Up first, the winners for contests 1-50. #1. Episode 10.23 – “Brother’s Keeper” Winner – guest #2 Episode 9.20 – “Bloodlines” Winner – Jen #3 Episode 8.12 – “As Time…
It’s that time of week again. The time to celebrate some wins then move onto the next game! I’m not sure how well I can top Nate’s Mother’s Day edition from last week, but I’ll give it my best. First, we have a double winner. Congrats to cheryl42! You’ve got the winning entries for both…
Time again for another contest! Apologies for being a day late, but well, you know, real life. So, I was struggling with picking a winner. I’d been following the entries, and as usual I enjoyed seeing the creativity, but I didn’t feel anything submitted captured the true essence of this scenic screencap. Then, on…
Weird. I can’t seem to find any winners. Ok I kid. Leave us I.T. our tacky jokes. The REAL winner for the Dean entry, is the site’s beloved stray, AlyCat22. And for the Sam entry, Marion had quite the winner this time around. Gratz all! So to finish out the year, and give you extra…
Welcome to the greatest game on Earth – WFB’s Caption this! First up, a big shout out to last week as you did your jobs and made it really tough for me to pick a winner. I do want to give kudos to cheryl42, who loves to add gifs and memes to her captions, and…
It’s the beginning of the week, it must be time for another Caption This! contest. Nate certainly gave you all a run for your money with last week’s selection. I think it perplexed most. The entries were certainly lighter than usual. While Nate can’t turn down some good toilet humor, I tend to favor…
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