<!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>I Kissed Drew Barrymore (Twice)</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 async src="https://www.caffeine.tv/embed.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push(function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("authorId","61920"),htlbid.setTargeting("tags",["sfw","drew-barrymore","sundae-converstion"]),htlbid.setTargeting("Verity_keywords",["drew barrymore","twice","| barstool sports","ed norton","adam sandler","jimmy fallon","queen","happiness","matthew mcconaughey","friggen fantastic thanks","highly","video","goddamn ball","ben stiller","watch"]),htlbid.setTargeting("Verity_IABv1",["IAB1"]),htlbid.setTargeting("Verity_IABv2",["432"]),htlbid.setTargeting("Verity_IABv3",["432"]),htlbid.setTargeting("Verity_positive","0.27"),htlbid.setTargeting("Verity_neutral","0.73"),htlbid.setTargeting("Verity_GGT5_conf","HIGH"),htlbid.setTargeting("Verity_GGT5_risk","HIGH"),htlbid.setTargeting("is_testing","no"),htlbid.pubads().setPublisherProvidedId("PPID-GOES-HERE"),htlbid.layout()})</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><script>window.htlAdUnitPath="57249056/in-app-iOS/Article-Page_In-Article-Unit",window.htlKeyvalues={authorId:"61920",category:"New York",tags:["sfw","drew-barrymore","sundae-converstion"],brandName:null,brandId:0,pagetype:"standard_post"}</script></head><body class="union__content"><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/437OURn?_showcaption=true" href="https://www.youtube.com/watch?v=JIGXvwVJWfc&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p>What do Matthew McConaughey, Adam Sandler, ED Norton, Jimmy Fallon, Ben Stiller, and myself all have in common? We have now been on-screen love interests of Drew Barrymore...which is no big deal and totally won't continuing mentioning it for the rest of my days AT ALL. My grandchildren are going to absolutely love that story. They're gonna eat it. I just know it. </p><p>In all seriousness though, this video was friggen fantastic thanks to not only Caleb being hilarious as always, but Drew just being a goddamn ball of happiness. What a queen. HIGHLY suggest you give it a watch. See y'all next Sunday!!</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/QRfu1Y5?_showcaption=true" href="https://www.instagram.com/p/CnvD3tjqxrx/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>And in the title when I said twice...I meant twice!!!</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/rtj6MHh?_showcaption=true" href="https://www.instagram.com/p/Cnww3q3OiCp/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p></p></body></html>

<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/437OURn?_showcaption=true" href="https://www.youtube.com/watch?v=JIGXvwVJWfc&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p>What do Matthew McConaughey, Adam Sandler, ED Norton, Jimmy Fallon, Ben Stiller, and myself all have in common? We have now been on-screen love interests of Drew Barrymore...which is no big deal and totally won't continuing mentioning it for the rest of my days AT ALL. My grandchildren are going to absolutely love that story. They're gonna eat it. I just know it. </p><p>In all seriousness though, this video was friggen fantastic thanks to not only Caleb being hilarious as always, but Drew just being a goddamn ball of happiness. What a queen. HIGHLY suggest you give it a watch. See y'all next Sunday!!</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/QRfu1Y5?_showcaption=true" href="https://www.instagram.com/p/CnvD3tjqxrx/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>And in the title when I said twice...I meant twice!!!</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/rtj6MHh?_showcaption=true" href="https://www.instagram.com/p/Cnww3q3OiCp/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p></p>

I Kissed Drew Barrymore (Twice)

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<!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>I Kissed Drew Barrymore (Twice)</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 async src="https://www.caffeine.tv/embed.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push(function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("authorId","61920"),htlbid.setTargeting("tags",["sfw","drew-barrymore","sundae-converstion"]),htlbid.setTargeting("Verity_keywords",["drew barrymore","twice","| barstool sports","ed norton","adam sandler","jimmy fallon","queen","happiness","matthew mcconaughey","friggen fantastic thanks","highly","video","goddamn ball","ben stiller","watch"]),htlbid.setTargeting("Verity_IABv1",["IAB1"]),htlbid.setTargeting("Verity_IABv2",["432"]),htlbid.setTargeting("Verity_IABv3",["432"]),htlbid.setTargeting("Verity_positive","0.27"),htlbid.setTargeting("Verity_neutral","0.73"),htlbid.setTargeting("Verity_GGT5_conf","HIGH"),htlbid.setTargeting("Verity_GGT5_risk","HIGH"),htlbid.setTargeting("is_testing","no"),htlbid.pubads().setPublisherProvidedId("PPID-GOES-HERE"),htlbid.layout()})</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><script>window.htlAdUnitPath="57249056/in-app-iOS/Article-Page_In-Article-Unit",window.htlKeyvalues={authorId:"61920",category:"New York",tags:["sfw","drew-barrymore","sundae-converstion"],brandName:null,brandId:0,pagetype:"standard_post"}</script></head><body class="union__content"><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/437OURn?_showcaption=true" href="https://www.youtube.com/watch?v=JIGXvwVJWfc&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>What do Matthew McConaughey, Adam Sandler, ED Norton, Jimmy Fallon, Ben Stiller, and myself all have in common? We have now been on-screen love interests of Drew Barrymore...which is no big deal and totally won't continuing mentioning it for the rest of my days AT ALL. My grandchildren are going to absolutely love that story. They're gonna eat it. I just know it. </p><p>In all seriousness though, this video was friggen fantastic thanks to not only Caleb being hilarious as always, but Drew just being a goddamn ball of happiness. What a queen. HIGHLY suggest you give it a watch. See y'all next Sunday!!</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/QRfu1Y5?_showcaption=true" href="https://www.instagram.com/p/CnvD3tjqxrx/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p>And in the title when I said twice...I meant twice!!!</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/rtj6MHh?_showcaption=true" href="https://www.instagram.com/p/Cnww3q3OiCp/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p></p></body></html>

<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/437OURn?_showcaption=true" href="https://www.youtube.com/watch?v=JIGXvwVJWfc&utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div><div id="Article-Ad-Placeholder" data-union-ad></div></div><p>What do Matthew McConaughey, Adam Sandler, ED Norton, Jimmy Fallon, Ben Stiller, and myself all have in common? We have now been on-screen love interests of Drew Barrymore...which is no big deal and totally won't continuing mentioning it for the rest of my days AT ALL. My grandchildren are going to absolutely love that story. They're gonna eat it. I just know it. </p><p>In all seriousness though, this video was friggen fantastic thanks to not only Caleb being hilarious as always, but Drew just being a goddamn ball of happiness. What a queen. HIGHLY suggest you give it a watch. See y'all next Sunday!!</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/QRfu1Y5?_showcaption=true" href="https://www.instagram.com/p/CnvD3tjqxrx/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p>And in the title when I said twice...I meant twice!!!</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/rtj6MHh?_showcaption=true" href="https://www.instagram.com/p/Cnww3q3OiCp/?utm_source=barstoolsports&utm_medium=referral&utm_content=blog&utm_term=61920_0_i-kissed-drew-barrymore-twice&utm_campaign=barstoolsports_referral_blog_61920_0_i-kissed-drew-barrymore-twice"></a></div></div></div><p></p>

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I Kissed Drew Barrymore (Twice)