・Ray O'Leary 2025 Melbourne International Comedy Festival Gala ▶3:58
・Preview: Your Laughter Is Just Making Me Stronger | Ray O'Leary ▶1:21
・Ray O'Leary – Comedy Up Late 2023 Melbourne International Comedy Festival ▶7:12
・Every time I've had fun | Ray O'Leary *rayoleary *comedy *shortscomedy ▶0:22
・Ray O'Leary - Mattress Protector 2024 Melbourne International Comedy Festival Gala ▶3:45
・Moving Apartment | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts *shortscomedy ▶0:52
・Ray O'Leary — Your Laughter Is Just Making Me Stronger (Full Comedy Special) 2025 ▶48:56
・Every time you laugh it adds a calorie | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts ▶1:14
・Are you going good? | Ray O'Leary 7 Days NZ *rayoleary *comedy *shortscomedy *comedyshorts ▶0:55
・You've Got My Vote | Ray O'Leary ▶0:28
・Comedy is going well | Ray O'Leary ▶0:10
・I don't really trouble myself with the score | Ray O'Leary @hybpa *comedyshorts *comedy *rayoleary ▶1:08
・"Ray's such a cool vegan" | Ray O'Leary ▶0:59
・Taskmaster NZ: Make this teenager think you're cool | Ray O'Leary ▶2:22
・Autism Awareness | Ray O'Leary ▶1:01
・My Roman Empire | Ray O'Leary 7 Days NZ *rayoleary *comedy *shortscomedy *comeyshorts ▶0:45
・Nothing manlier than being in a band called Queen | Ray O'Leary @7daysnz *rayoleary *comedy *funny ▶0:24
・Preparing to go on a roller coaster | Ray O'Leary ▶1:22
・Pronunciation Matters | Ray O'Leary *shortscomedy *rayoleary *comedyshorts *nzcomedy ▶0:30
・Taskmaster NZ: Cross Behind the Screen | Ray O'Leary *taskmaster *taskmasternz *rayoleary *comedy ▶0:37
・Discover Stand Up Comedy Highlights at Melbourne Comedy Festival ▶1:00
・Ray O'Leary on Instagram: "Would you steal a loaf of bread to feed your family? I would, but I would pick a much weaker, needier family to steal from. Full special available to stream on YouTube now, bread available from whoever you think you could defeat in a fight *comedyreels *rayoleary" ▶0:54
・Crack the Code: Unveiling the Intricacies of the 7 Days Game ▶0:41
・Ray O'Leary on Instagram: "Become another contestant. Best becoming of another contestant wins. If you become the same contestant as someone else, your points will be halved. You must emerge through a door as your chosen contestant in twenty minutes. Your time starts now *taskmaster *rayoleary" ▶0:43
・Guess By Feel | Ray O'Leary - Guy Montgomery's Guy Mont-Spelling Bee ▶2:19
・Replying to @psibreaker we have never laughed so hard 😂 *taskmaster *taskmasternz *taskmasternewzealand *bubbah *melbracewell *karenoleary *rayoleary *daihenwood ▶1:14
・Taskmaster Game: Fastest to Lie Down Challenge ▶1:39
・rayolearycomedy on TikTok ▶0:41
・Ray O'Leary on Instagram: "Fastest to lie down wins. Your time started when you began reading the task *taskmaster *rayoleary" ▶1:16
・Ray O'Leary on Instagram: "I just think it's unacceptable that artists think they can get away with that. You can see the actual end to the show, and the beginning, and even some more of the middle by going to YouTube and watching "Your Laughter Is Just Making Me Stronger" *comedyreels *rayoleary" ▶0:44
・The Saddest Kids Party Balloon Blow Up Challenge ▶1:58
・Ray O'Leary on Instagram: "I got given the opportunity to go on Australian television and I spent 4 minutes talking about linen *rayoleary *standupcomedy" ▶0:57
・Ray O'Leary on Instagram: "Still waiting on that desk. From my special "Your Laughter Is Just Making Me Stronger" which you can watch for free right now on YT *comedyreels *rayoleary" ▶1:30
・Acceptance Speech Trophy Challenge ▶1:16
・rayolearycomedy on TikTok ▶2:10
・Make a bet with Paul and win. Pokemon is life. *taskmaster *taskmasternz *taskmasternewzealand *taskmasterclips *taskmasterau *rayoleary *pokemon *pokemongo *pokemontiktok *pokemoncommunity @Taskmaster @TaskmasterNZ @Paul Williams *taskmasteredit ▶0:29
・Surgical Scrubs Balloon Challenge ▶0:44
・I don't do well in job interviews | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts ▶0:45
・I asked 5 different spray tan places and they all said no. *taskmasternz Greatest Orange Thing *taskmasternewzealand *taskmaster *rayoleary ▶0:43
・Taskmaster NZ: Find Your Doppelgänger ▶0:31
・Ray O'Leary on Instagram: "Pronunciation matters *rayoleary *comedy" ▶1:15
・Cricket Challenge: Knock the Bails Off from a Distance ▶0:18
・Ray O'Leary on Instagram: "I'm just finding out now?! *MICF @melbcomedyfestival *rayoleary" ▶1:05
・Ray O'Leary on Instagram: "Why is tipping culture spreading outside of America? This clip is from a special you can watch for free on YouTube right now, no tipping required *comedyreels *rayoleary *standupcomedy" ▶1:00
・Beauty and the geek 🤓 *rayoleary *hybpa *beautyandthegeek *geek *newzealand *nzcomedy @*HYBPA ▶1:14
・Ray O'Leary on Instagram: "Now when someone leaves me on seen I assume this is why. I have observed more things and made comedic musings about them in the full show available for free on YT right now *comedyreels *comedyvideo *rayoleary" ▶0:46
・Ray O'Leary on Instagram: "I went to New Zealand and all I got was roasted by the mayor of Auckland *7DaysNZ *rayoleary" ▶0:46
・Neighbor Recording His Neighbor - Hybpa *hybpa *rayoleary ▶7:15
・rayolearycomedy on TikTok ▶0:29
・Taskmaster Prize Task: Most Unbelievable Thing Revealed by Ray O'Leary ▶0:32
・Funny Hotel Moments with Ray O'Leary: Overheard Stories and Wake-Up Calls ▶0:13
・I Hate My Mattress Protector | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts ▶0:30
・Spell an audience member's name | Ray O'Leary - Guy Montgomery's Guy Mont-Spelling Bee ▶0:17
・Egg Compliment Challenge: Taskmaster NZ Game Show ▶0:39
・Discovering Australian Sports: Embracing the St. Kilda Saints ▶1:04
・I hate tipping at restaurants | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts ▶0:43
・Ray O'Leary 2023 Sydney Comedy Festival ▶0:17
・Comedy Vs Philosopy | Ray O'Leary *standupcomedy *rayoleary *shortscomedy *comedyshorts ▶0:34
・Ray O'Leary on Instagram: "Bring in the best gift for your 12 year old self *taskmaster *rayoleary" ▶0:32
・Ray O'Leary on Instagram: "My parents reaction to me wanting to be a comedian. Did I ever become a comedian? The only way to find out is by watching my new special out now YouTube *rayoleary *comedyreels" ▶1:00
・?? @hybpa_nz *hybpanz *HYBPA *rayoleary ▶1:21
・Examples of Angry Nurses and the World's Worst Weather Reporters ▶0:42
・Ray O'Leary on Instagram: "Congrats to the happy couple *rayoleary" ▶0:21
・Men in Suits: Taskmaster Compilation ▶0:41
・Ray O'Leary on Instagram: "Use this entire roll of Sellotape in the most brilliant way. You cannot waste any of it. Most brilliant use of the entire roll of sellotape wins. You have twenty minutes. Your time starts now *taskmaster *rayoleary" ▶4:17
・Blow out the candle in the most bold and beautiful way. You cannot use your lungs. Most bold and beautiful blowout wins. You have fifteen minutes or until the candle is blown out. Your time started when you entered the room *taskmaster *rayoleary ▶0:58
・rayolearycomedy (@rayolearycomedy) - Balloon Blowing Practice - Taskmaster Training ▶0:32
・Ray O'Leary on Instagram: "Nothing manlier than being in a band called Queen *7DaysNZ *rayoleary *comedyreels" ▶0:41
・Ray O'Leary on Instagram: "Bring in the best thing that reminds you of home *taskmaster *rayoleary" ▶0:22
・Chris Hipkins' visit to China @7days_nz *rayoleary ▶0:43
・Taskmaster NZ: Create a Podcast *taskmaster *taskmasternz *rayoleary *melaniebracewell *tmnz ▶0:37
・A Stranger's Diagnosis | Ray O'Leary *standupcomedy *shortscomedy *rayoleary *micf ▶0:56
・Some Jokes About Hair | Ray O'Leary ▶0:59
・Ray O'Leary on Instagram: "I would make fun of Americans less if they stopped commenting on my videos calling me British *spellingbee *rayoleary" ▶0:59
・How to Enjoy Croissants Like a Pro ▶0:52
・Taskmaster Clips and TV Series ▶0:46
・Ray O'Leary - Crazy Beliefs - Best Foods Comedy Gala 2023 ▶1:04
・Bring in the most braggable item | Ray O'Leary *taskmaster *rayoleary ▶0:41
・Taskmaster NZ: Improve Paul | Ray O'Leary *taskmaster *taskmasternz *rayoleary *comedy *shortscomedy ▶1:01
・rayolearycomedy on TikTok ▶4:47
・Does my suit suit? | Ray O'Leary ▶0:43
・My tip to help the environment | Ray O'Leary *standupcomedy *rayoleary *comedy *shortscomedy ▶0:28
・The Wiggles in Therapy | Ray O'Leary 7 Days NZ *rayoleary *comedy *comedyshorts *shortscomedy ▶1:07
・Ray O'Leary on Instagram: "Hi-diddly-ho, neighborino  *hybpa *rayoleary *comedy" ▶0:47
・Genius 😂 ▶1:20
・Soviet Union Spelling Bee Challenge with Guy Montgomery - Funny Video ▶0:18
・Dispelling the Old Wives Tale about Sitting Close to the TV ▶4:23
・Ray O'Leary and Emma Holland's Surprising Hangout | Comedy Show Drama ▶1:25
・Taskmaster NZ: Blow Out The Candle | Ray O'Leary ▶0:16
・Ray O'Leary on Instagram: "I still think about how different my life could've been if I had just ridden that rollercoaster *comedyreels *comedyvideo *rayoleary" ▶2:15
・rayolearycomedy on TikTok ▶
・I bought a mattress protector and I have to tell you about it because the only one you'd know if anyone had a mattress protector is if they told you. Full special available to stream on YouTube now, and available to watch from the comfort of your own mattress *rayoleary *standupcomedy ▶
・rayolearycomedy on TikTok ▶
・Too dangerous to own a desk | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts ▶
・Ray O'Leary On Why He Loves The Music Of Glee So Much ▶
・Pillows without the case | Ray O'Leary *standupcomedy *rayoleary *shortscomedy ▶
・Still waiting for the day there is an emergency where I can use my philosophy degree @7days_nz *rayoleary ▶
・My Philosophy? | Ray O'Leary *standupcomedy *comedyshorts *rayoleary *shortscomedy ▶
・Major Career Setback | Ray O'Leary *standupcomedy *rayoleary *shortscomedy *comedyshorts ▶
・Haunted by a Roller Coaster | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts ▶
・I've just found out I'm 18 years old | Ray O'Leary *7daysNZ *standupcomedy *comedy *shortscomedy ▶
・Ray O'Leary: The Big Problem With Bedroom Pillows ▶
・Lazy Songwriting | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts ▶
・Do you guys like impressions? | Ray O'Leary *comedy *rayoleary *standupcomedy *comedyshorts *funny ▶
・Ray O'Leary on TikTok ▶

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