Barstool Chicago

<!DOCTYPE html><html lang="en"><head><meta charset="utf-8"><meta name="viewport" content="width=device-width,initial-scale=1,maximum-scale=1,user-scalable=no,shrink-to-fit=no"><title>Guess That Ass</title><link rel="stylesheet" type="text/css" href="https://htlbid.com/v3/barstoolsports.com/htlbid.css"><script async src="https://htlbid.com/v3/barstoolsports.com/htlbid.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push((function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("brandId","61"),htlbid.setTargeting("authorId","63538"),htlbid.setTargeting("tags",["gta","guess-that-ass","britney","spears","britney-spears","vacation"]),htlbid.setTargeting("Verity_keywords",["ass | barstool sports","ass","plenty","island life","giphy images","pov videos","creepy dad","vacation","drill","ms. spears","awful lot","answer","favorite game","blog","time"]),htlbid.setTargeting("Verity_positive","0.5"),htlbid.setTargeting("Verity_neutral","0.5"),htlbid.setTargeting("Verity_GGT5_conf","VERY_HIGH"),htlbid.setTargeting("Verity_GGT5_risk","HIGH"),htlbid.setTargeting("Verity_GGT4_conf","VERY_HIGH"),htlbid.setTargeting("Verity_GGT4_risk","HIGH"),htlbid.setTargeting("is_testing","no"),htlbid.layout()}))</script><script>var googletag = googletag || {};
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        pbjs.setConfig({ pageUrl: https://www.barstoolsports.com/blog/3403425/guess-that-ass });</script><script src="https://d9rde3y35j061.cloudfront.net/script.js"></script><script src="https://htlbid.com/v3/barstoolsports.com/htlbid.js" async></script><script src="https://iframely.barstoolsports.com/embed.js" async></script><style>.union__content{font-family:-apple-system,HelveticaNeue,Roboto,sans-serif;font-weight:400;font-size:18px;color:#5a5b5d;word-wrap:break-word;box-sizing:border-box;padding:0 5px 32px 5px}.union__content p{padding:0;margin:16px 0 0 0}.union__content img{display:block;width:100%!important;height:auto;margin:16px 0 0 0}.union__content video{display:block!important;width:100%!important;height:auto;margin:16px 0 0 0}.union__content .articleAd{text-align:center;margin:16px 0 0 0;background-color:#f5f5f5}.union__content .htlad__container{display:inline-block}.union__content p a{color:#377dc4}.union__content .oembed__wrapper{margin:16px 0 0 0}.union__content blockquote:not(.twitter-video){display:block;margin:16px 0 0 0;padding:4px 12px;border-left:4px solid #77889a;font-style:italic;background:#f0f4f8;text-align:left;border-radius:0 6px 6px 0}.union__content blockquote:not(.twitter-video) p{font-style:italic}.union__content blockquote,q{quotes:none}.union__content iframe{max-width:100%}.union__content .bs-image-hidden{display:none}.union__content div.hq-image{width:fit-content;margin:0 auto}.union__content span.image-attribution,.union__content span.image-attribution a{color:#757575;font-size:12px;font-style:italic;letter-spacing:.1px;line-height:14px;text-decoration:none;padding:0;margin:0}.union__content .bs-videoPlayer .bs-videoPlayer__container,.union__content video-js,.wp-video{width:100%!important;height:0!important;position:relative;padding-bottom:56.25%;overflow:hidden;margin:16px 0 0 0}.wp-video video{width:100%!important;height:100%!important}.hq-image video{width:100%!important;height:100%!important}.union__content .bs-videoPlayer__container>iframe{position:absolute;top:0;left:0;width:100%;height:100%;border:none}@media (prefers-color-scheme:dark){.union__content,body,html{background:#1c1c1c;color:#f1f1f1}.union__content blockquote:not(.twitter-video){border-left:4px solid #367dc4;background:#272c35}}</style><script>window.addEventListener("applicationDidBecomeActive",(()=>{document.querySelectorAll(".hq-image video[autoplay]").forEach((e=>e.play()))}))</script></head><body class="union__content"><p>It's once again time for everybody's favorite game. </p><p>You know the drill.</p><p><img src="https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" class="fr-fic fr-dib bs-image" draggable="true" alt data-image-provider data-image-author data-image-direct data-image-tracking data-image-id="MQMLSejizRjBagca6bNgPO36" srcset="https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 776px" loading="eager" style="aspect-ratio:1.5887445887445888;width:100%"></p><p>Who you got?</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>Drum roll please…</p><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>And the answer is -</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=jpg" type="image/jpeg"></video><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span></div><p>You bet your ass it is.</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/TAKleIT?_showcaption=true" href="https://www.instagram.com/p/CZIpJBhPmNO/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/PPnfWA1?_showcaption=true" href="https://www.instagram.com/p/CZK4PN_smLo/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><p>Ms. Spears has been living an awful lot of the the island life on vacation lately and I couldn't be happier for her. She deserves it.</p><p>Also, love that she's supplying her creepy dad with plenty of POV videos like these to satiate him now that he can't record her himself. (Shameless plug for the blog I wrote)</p><p> </p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/1JLCQFr?_showcaption=true" href="https://www.barstoolsports.com/blog/3402819/britney-spears-father-might-be-the-creepiest-dude-on-the-planet-an-fbi-agent-confirmed-he-had-her-bedroom-bugged-and-had-surveillance-cameras-hidden-in-her-hotel-rooms?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>Here's more Britney</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/NTL4kSG" 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<p>It's once again time for everybody's favorite game. </p><p>You know the drill.</p><p><img src="https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" class="fr-fic fr-dib bs-image" draggable="true" alt data-image-provider data-image-author data-image-direct data-image-tracking data-image-id="MQMLSejizRjBagca6bNgPO36" srcset="https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 776px" loading="eager" style="aspect-ratio:1.5887445887445888;width:100%"></p><p>Who you got?</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>Drum roll please…</p><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>And the answer is -</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=jpg" type="image/jpeg"></video><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span></div><p>You bet your ass it is.</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/TAKleIT?_showcaption=true" href="https://www.instagram.com/p/CZIpJBhPmNO/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/PPnfWA1?_showcaption=true" href="https://www.instagram.com/p/CZK4PN_smLo/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><p>Ms. Spears has been living an awful lot of the the island life on vacation lately and I couldn't be happier for her. She deserves it.</p><p>Also, love that she's supplying her creepy dad with plenty of POV videos like these to satiate him now that he can't record her himself. (Shameless plug for the blog I wrote)</p><p> </p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/1JLCQFr?_showcaption=true" href="https://www.barstoolsports.com/blog/3402819/britney-spears-father-might-be-the-creepiest-dude-on-the-planet-an-fbi-agent-confirmed-he-had-her-bedroom-bugged-and-had-surveillance-cameras-hidden-in-her-hotel-rooms?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>Here's more Britney</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/NTL4kSG" 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.bs-videoPlayer__container>iframe{position:absolute;top:0;left:0;width:100%;height:100%;border:none}@media (prefers-color-scheme:dark){.union__content,body,html{background:#1c1c1c;color:#f1f1f1}.union__content blockquote:not(.twitter-video){border-left:4px solid #367dc4;background:#272c35}}</style><script>window.addEventListener("applicationDidBecomeActive",(()=>{document.querySelectorAll(".hq-image video[autoplay]").forEach((e=>e.play()))}))</script></head><body class="union__content"><p>It's once again time for everybody's favorite game. </p><p>You know the drill.</p><p><img src="https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" class="fr-fic fr-dib bs-image" draggable="true" alt data-image-provider data-image-author data-image-direct data-image-tracking data-image-id="MQMLSejizRjBagca6bNgPO36" 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https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 776px" loading="eager" style="aspect-ratio:1.5887445887445888;width:100%"></p><div id="Article-Ad-Placeholder" data-union-ad></div><p>Who you got?</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>Drum roll please…</p><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span></div><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>And the answer is -</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=jpg" type="image/jpeg"></video><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span></div><p>You bet your ass it is.</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/TAKleIT?_showcaption=true" href="https://www.instagram.com/p/CZIpJBhPmNO/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/PPnfWA1?_showcaption=true" href="https://www.instagram.com/p/CZK4PN_smLo/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>Ms. Spears has been living an awful lot of the the island life on vacation lately and I couldn't be happier for her. She deserves it.</p><p>Also, love that she's supplying her creepy dad with plenty of POV videos like these to satiate him now that he can't record her himself. (Shameless plug for the blog I wrote)</p><p> </p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/1JLCQFr?_showcaption=true" href="https://www.barstoolsports.com/blog/3402819/britney-spears-father-might-be-the-creepiest-dude-on-the-planet-an-fbi-agent-confirmed-he-had-her-bedroom-bugged-and-had-surveillance-cameras-hidden-in-her-hotel-rooms?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><p>Here's more Britney</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/NTL4kSG" href="https://www.instagram.com/p/CVv1YHgB3aU/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/uksamTX" href="https://www.instagram.com/p/CVodiFusAHa/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/9eyTuwr" href="https://www.instagram.com/p/CVB45NwpYlg/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/A8fPExx" href="https://www.instagram.com/p/CUoG2rppHHJ/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/ROYie6l" href="https://www.instagram.com/p/CUdtzpSvlOJ/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/aRYLt9Z" href="https://www.instagram.com/p/CTxoSzqD-TL/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/Kjjofk2" href="https://www.instagram.com/p/CTnk-DMP4xi/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/nHn4PB8" href="https://www.instagram.com/p/CTnpGg6DKfl/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/GcHTvXr" href="https://www.instagram.com/p/CTnfzX5PWv_/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/Rde3FUk" href="https://www.instagram.com/p/CR2ABVkAcGs/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/ayVLqFl" href="https://www.youtube.com/watch?v=tkmFoOfrewI&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/bymAQ8Y" href="https://www.youtube.com/watch?v=BOKCzZbmaTM&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/b158La6" href="https://www.youtube.com/watch?v=GwO1wtmVsc8&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/0yi07jC" href="https://www.youtube.com/watch?v=AMxHz0TYo7c&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/5aKzS51" href="https://www.youtube.com/watch?v=66Q9sk2KIF8&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p></p></body></html>

<p>It's once again time for everybody's favorite game. </p><p>You know the drill.</p><p><img src="https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" class="fr-fic fr-dib bs-image" draggable="true" alt data-image-provider data-image-author data-image-direct data-image-tracking data-image-id="MQMLSejizRjBagca6bNgPO36" srcset="https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2022/01/25/Screen-Shot-2022-01-25-at-6.52.41-PM.5e149de6.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 776px" loading="eager" style="aspect-ratio:1.5887445887445888;width:100%"></p><div id="Article-Ad-Placeholder" data-union-ad></div><p>Who you got?</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>Drum roll please…</p><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2021/12/21/885f99e1.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span></div><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>And the answer is -</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><p>.</p><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/2022/01/25/michael-scott-its-britney-bitch.44207333.gif?format=jpg" type="image/jpeg"></video><div class="hq-image"><video autoplay loop muted playsinline alt><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=mp4&profile=high&level=5.0" type="video/mp4"><source src="https://chumley.barstoolsports.com/union/giphy/2022/01/25/5763cf32.gif?format=jpg" type="image/jpeg"></video><span class="image-attribution">Giphy Images.</span></div><p>You bet your ass it is.</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/TAKleIT?_showcaption=true" href="https://www.instagram.com/p/CZIpJBhPmNO/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/PPnfWA1?_showcaption=true" href="https://www.instagram.com/p/CZK4PN_smLo/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>Ms. Spears has been living an awful lot of the the island life on vacation lately and I couldn't be happier for her. She deserves it.</p><p>Also, love that she's supplying her creepy dad with plenty of POV videos like these to satiate him now that he can't record her himself. (Shameless plug for the blog I wrote)</p><p> </p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/1JLCQFr?_showcaption=true" href="https://www.barstoolsports.com/blog/3402819/britney-spears-father-might-be-the-creepiest-dude-on-the-planet-an-fbi-agent-confirmed-he-had-her-bedroom-bugged-and-had-surveillance-cameras-hidden-in-her-hotel-rooms?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=63538_61_guess-that-ass&utm_campaign=barstoolsports_referral_blog_63538_61_guess-that-ass"></a></div></div></div><p>Here's more Britney</p><div class="oembed__wrapper"><div class="iframely-embed" style="max-width:550px"><div class="iframely-responsive" style="padding-bottom:100%"><a data-iframely-url="https://iframely.barstoolsports.com/NTL4kSG" 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