Win Tickets ($70): Ben Bailey @ Crystal Ballroom | Cash Cab, Comedy

We are giving away a pair of tickets to Ben Bailey @ Crystal Ballroom on September 30. To win, comment below on this post why you’d like to attend. Winner will be drawn and emailed September 25.


From our sponsors:
Ben Bailey
Robby Sherman

September 30, 2023
Doors 6:30PM, Show 8PM | $30 ADV, $35 Doors | 21+
More info:

Crystal Ballroom
1332 W Burnside St, Portland, OR 97209

Long before he got behind the wheel of “Cash Cab,” Ben Bailey left his home in a small town in New Jersey and headed to Los Angeles to pursue his dream of a career in show business. Six weeks later he found himself on stage at The Comedy Store. Shortly thereafter, Bailey returned to the East Coast and started hanging out at the comedy clubs in New York City. He quickly became a crowd favorite and has since performed at all the major festivals – Montreal and Chicago (Just for Laughs), the (hallowed and former) Aspen Comedy Arts Festival and The Edinburgh Fringe Festival – as well as at clubs and theaters around the world.

By 2005, Bailey had appeared in several commercials, on Fox’s “MADtv” and became a regular on “Tough Crowd with Colin Quinn.” He also made stand up appearances on HBO, NBC, “Star Search,” “Last Call with Carson Daly” and “The Late Show.”

Bailey drove the smash hit series “Cash Cab” (still in syndication around the world) for over 550 episodes. The show ran from 2005-2012 and again from 2017-2019 ( Bailey was nominated four times for the Daytime Emmy Award for Outstanding Game Show Host, winning the award in 2010, 2011 and 2013. “Cash Cab” won the Daytime Emmy Award for Outstanding Game Show in 2008, 2009 and 2010. In 2013, the show appeared in TV Guide’s list of the 60 greatest game shows ever.

He’s also hosted several other TV shows – including NBC’s “Who’s Still Standing,” “Best in The Business,” Discovery’s “After the Catch” and NatGeo’s “Brain Games” – and appeared in multiple pilots.




  1. Ben on March 20, 2023 at 9:03 pm

    Ben is hilarious! Would love to see this!

    • Bradlee Webber on March 22, 2023 at 7:01 am

      I would love to see this! He is great! I want to take my friend Michelle so she will smile and laugh out loud! 😂 (Lol)

    • Rachel Proper on July 18, 2023 at 10:54 pm

      Ben Bailey. Fuck yeah! Please please please…me luv you long-time whether u send me n my most awesome roomie tickets or not. They would be ever SO APPRECIATED! This would mean the world to my roomie for he loves Ben Bailey n so do i!!! Have a great day n thanks for having contests so your readers have a chance♡

  2. Brent Headrick on March 21, 2023 at 1:35 pm

    This guy is hilarious

  3. Maria on March 21, 2023 at 3:50 pm

    OH MY GOSH!!! I would love to be considered to see this handsome guy in person. I have always watched Cash Cab. Well when it was playing. But to see him in person.. that would just be awesome. He is so hilarious too.
    Thank you in advance!

  4. Andi on March 21, 2023 at 4:35 pm

    This would be a hoot to see him in person.

  5. Amber on March 21, 2023 at 5:01 pm

    This would be SO fun to see in person, I am a Cash Cab fanatic!

  6. Ryan Jones on March 21, 2023 at 8:57 pm


    • Trill on March 23, 2023 at 6:51 am

      I would love to see Ben

    • Holly on August 15, 2023 at 2:47 pm

      Sounds fun

  7. Jim Winski on March 21, 2023 at 8:57 pm

    OMG yes!

  8. Teena Winski on March 21, 2023 at 8:58 pm

    I love comedy and could use a laugh 😉

  9. Alice Jones on March 21, 2023 at 8:59 pm

    Would love to go!

  10. Claudia on March 22, 2023 at 7:23 am

    Yes, please!!! Such a hilarious human 😆

  11. B. Anders on March 22, 2023 at 2:19 pm

    Ben Bailey, who else has he been?

  12. steadycab on March 22, 2023 at 4:29 pm

    Ben from cash cab–uber stoked!

  13. Carolyn Allen on March 24, 2023 at 10:47 am

    Never will I likely ever get in a cab with Ben, but I could LMAO for a night in Portland! ✌️💜

  14. Jake J on March 24, 2023 at 8:20 pm

    Would love to see Ben live!

  15. Heather Summers on March 25, 2023 at 12:33 pm

    Sounds amazing!!!

  16. Cory on March 25, 2023 at 2:28 pm

    Cabin it

  17. Brent on March 28, 2023 at 12:53 pm

    Benny B is the place to be!

  18. Kelly on March 28, 2023 at 8:32 pm

    It may not be as cool as hopping into a cab and winning money, but I’d happily take the Max to the Crystal and feel like a true winner if PDX Pipeline picks me

  19. Mikel on March 30, 2023 at 1:45 pm

    Would be awesome to see him.

  20. Whitney on March 31, 2023 at 10:05 pm

    Always hoped I’d make it to NYC and catch the Cash Cab!! I think seeing Ben live in Portland is the next best thing 😛

    • Johanna on April 15, 2023 at 11:47 pm

      I need a good laugh!

  21. Sunny ☀️ on April 2, 2023 at 8:08 am

    💰 🚕 💛

  22. Juva on April 4, 2023 at 12:46 pm


  23. Danielle on April 5, 2023 at 10:39 am

    Would really enjoy checking out his show live.

  24. Natty O'Hare on April 9, 2023 at 10:15 pm

    Oh man, hope he borrows a Radio Cab!

  25. Drew on April 11, 2023 at 3:23 pm

    Ben Bailey is funny af. I loved Cash Cab

  26. Paula S on April 13, 2023 at 6:36 pm

    Hi It’s my Birthday month. I hope to be sent to all September’s events, or at least one. Love and peace. P

  27. Sam S on April 20, 2023 at 12:35 pm

    Yes! Ben would be a great time live.

  28. Naomi Tsai on April 27, 2023 at 4:37 pm

    Would love to see him!!!

  29. Harmony Byrne on April 30, 2023 at 2:15 pm

    Pick me🥹❣️

  30. Jessica Delta on May 2, 2023 at 1:21 pm

    I adored how kind and respectful he was on Cash Cab
    and PDX Pipeline ->Thanks for helping me find places to send my resume in PDX.

  31. Jennifer on May 2, 2023 at 3:12 pm

    I would love to deepen my laugh lines!

  32. Heather on May 2, 2023 at 4:22 pm

    I’d love to go!

  33. Tom Heaslet on May 2, 2023 at 8:30 pm

    Please let me in and I promise not to yell out WELCOME TO CASH CAB ! But on a more serious note Ben is funny and I would like to see him in person

  34. Jay on May 3, 2023 at 3:16 pm

    I would love to see a comedy show at the Crystal Ballroom, lets see if we can get the floor to belly laugh!

  35. Amber on May 3, 2023 at 3:30 pm

    I would love to see Ben in person!

  36. Brandie on May 3, 2023 at 9:44 pm

    OMG!! We would love to see him live

  37. Summer on May 6, 2023 at 10:17 am

    I haven’t laughed in 48 years.

  38. DawnF on May 6, 2023 at 7:44 pm

    Never been. Sounds fun!!!

  39. Heather on May 9, 2023 at 1:03 pm

    Ben B! OMG, this is going to be such a fun event!

  40. Lisa Kendall on May 9, 2023 at 2:43 pm

    I volunteer to address policy to prevent abuse to children in cults and could use a laugh!

    Lighten my load with a night of comedy.

  41. Lori Nye on May 9, 2023 at 7:57 pm

    I just turned 60. I need a gut busting, life-is-good, all is right in the world night of comedy. I know Ben can deliver that. Please, let me be the one.

  42. Kelsey on May 11, 2023 at 8:35 am

    Languish Laugh Loathe

  43. Christina on May 12, 2023 at 12:07 pm

    This would be AWESOME to go see!!!

  44. T Eva on May 18, 2023 at 4:37 am

    Love Ben, love the Crystal Ballroom. Sounds like an incredible night!

  45. BLU on May 19, 2023 at 7:05 am

    I would love to see Ben!

  46. Amy H. on May 19, 2023 at 5:48 pm

    Love a comedy show and love Ben, sign me up!

  47. Ashley R on May 23, 2023 at 1:55 pm

    A chance to see Mr. Cash Cab?! Sign me up!

  48. Jana Rocheleau on May 23, 2023 at 4:12 pm

    I would love to see Ben’s show! A good laugh is always good 🙂

    • Brett welches on July 18, 2023 at 12:21 pm

      Dudes not funny… hah

  49. Nicole SmithRyan on May 23, 2023 at 10:14 pm

    Let’s win some cash to see the cash cab!!

  50. Hannah on May 24, 2023 at 10:57 am

    I’ve loved Cash Cab and, subsequently Ben Bailey for over 14 years! Just sent this to my old college friend who would watch with me. It would be a trip to see him in person!

  51. Carolyn Ingram on May 30, 2023 at 1:04 pm

    Ben is a hoot! I used to luv watching Cash Cab! This would be a fun show!

    • Lourinda Dozier on June 15, 2023 at 3:29 pm

      Ben Bailey always brings a smile to my face!
      I love his humor ♥️ and would love to spend an evening laughing with Ben Bailey.
      Such a fun night!

  52. Steve Russell on May 30, 2023 at 5:21 pm

    Who doesn’t love a good laugh or a hundred?

    • Heather Roberts on May 31, 2023 at 6:29 am

      We’ll Yes Ben! I’d love to double up, go for broke and put it all on one last question.. “Alright”.. So here we go.
      Q: Who attended this show on September 30, 2023 at the crystal ballroom in Portland Oregon?
      Answer: Me, Me, Me..
      Let’s see if your correct…
      ? ?

  53. Patricia on June 4, 2023 at 1:06 pm

    Just keep laughing to prevent crying…

  54. Jacob on June 6, 2023 at 3:18 pm

    I haven’t seen him before. This would be fun to go to!

  55. Carl on June 6, 2023 at 3:40 pm

    Enjoyed his cash cab adventures and in reruns still make me laugh

  56. Heidi on June 6, 2023 at 3:44 pm

    He’s hilarious and I need a good laugh!

  57. Holly on June 6, 2023 at 8:43 pm

    Loved his show

  58. Jason Wilcox on June 9, 2023 at 5:54 pm

    Sheeit. I just circumcised my baby boy. May this dick relieve the pain of another (and his puking Daddy).

  59. Sunny ☀️ on June 20, 2023 at 7:06 pm

    ReadY 2 laugH LOUD!!! 🤣

  60. Mike on June 21, 2023 at 8:35 am

    Ready to laugh.

  61. ANGIE on June 21, 2023 at 10:26 am

    So fun to get to go!!

  62. Amy on June 22, 2023 at 2:41 pm

    Ben Bailey!! Yes, please!!

  63. shen on June 27, 2023 at 2:45 pm

    This would be so fun!

  64. Christina on July 5, 2023 at 12:45 am

    Ben was extremely funny on Cash Cab. Didn’t know he did stand up.

  65. Christina M on July 5, 2023 at 10:58 pm

    Loved his show as a kid!

  66. Joe Trekas on July 6, 2023 at 6:38 pm

    Would love to take my wife for our wedding anniversary.

  67. Mark on July 12, 2023 at 12:01 am

    Cash Van was awesome! Best quiz show ever. Would love to see him live.

  68. Austin Walker on July 18, 2023 at 10:12 am

    Would love to partner to this, just after their birthday!

  69. Kristina C on July 18, 2023 at 1:21 pm

    Sounds fun! We would love to go 🙂

  70. Dan on July 18, 2023 at 7:31 pm

    Would love to see him in an NYC cab but CBR in PDX would be just as good!

  71. Ken Cosey on July 24, 2023 at 8:30 pm

    Ben Bailey has “Ben” very funny for a long time! I would love to see him in person!

  72. Alex P. on July 25, 2023 at 10:33 am

    Loved Cash Cab, this would be great to win!

  73. Brig on July 26, 2023 at 8:15 am

    I like watching this guy on Cash Cab. Haven’t heard him do standup before. Looking forward to the opportunity!

  74. Heather on August 4, 2023 at 5:04 pm

    I would love to see Ben!

  75. Katie Sweeney on August 8, 2023 at 8:40 pm

    Cash Cab was one of mine and my mother’s favorite game shows growing up! Ben Bailey is hilarious. This show falls on my moms birthday weekend; I’d love to be able to surprise her!

  76. Carolyn Allen on August 10, 2023 at 3:57 pm

    This isn’t the cash me outside girls Uncle is it?? 🤣

  77. Tanja on August 11, 2023 at 6:43 pm

    It has been so long since I’ve actually really laughed cuz I’ve been to busy working my ass off and can’t afford a good laugh but desperately need and deserve one. Please pick me for free tickets

  78. Sarah Allen on August 22, 2023 at 1:21 pm

    Ben’s hilarious! This show’s going to be so good!!

  79. LIsa on August 23, 2023 at 11:46 am

    This would be great to see the Cash Cab dude live.

  80. Jake B. on August 24, 2023 at 1:06 pm

    Let’s go Ben! I want tix!

  81. Maggie on September 3, 2023 at 8:31 am

    Need a good laugh

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