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An Interview With Tim Dressen, Host of Five Hundy by Midnight

VHH chats with Tim Dressen, host of popular Las Vegas Podcast Five Hundy by Midnight

Anyone who has strolled the sidewalks of the glitzy Las Vegas Strip knows hotel executives do nearly anything to get warm bodies through the door. Where else is a $250 million resort considered dated despite being a shade older than the legal gambling age? The competition is fierce, and each hotel does what it must to keep a sliver of the spotlight. From tower additions and room remodels to rotating restaurant and nightclub collections, each destination is constantly adding a fresh coat of paint.

As soon as that paint dries (and sometimes before), it’s a sure bet that a media storm is soon to follow. Grand openings, re-openings, celebrity appearances and venue anniversaries all provide the perfect excuse to snap a few photos and push out a press release. In each piece, everything is made out to be the best thing since sliced bread. Who then, is there, then, to filter out the excess and cut straight to the point? Enter Five Hundy By Midnight – The Original Las Vegas Podcast.

An early adopter of the podcast craze, Tim Dressen created Five Hundy By Midnight in early 2005. A product of a personal fascination with Las Vegas and childhood radio aspirations, the self-noted Original Las Vegas Podcast is a (more or less) weekly audio show that covers all corners of Las Vegas tourism. Drawing its title from the 1996 cult comedy Swingers, the show has carved out a fun niche in Las Vegas lore, keeping Las Vegas enthusiasts entertained for more than 350 episodes spanning over seven years.

In every way that fellow Minnesotan audio show A Prairie Home Companion provides that cozy, at-home feeling of chatting with friends over a glass of wine, so too do Tim and Michele’s Five Hundy by Midnight. In their case however, the wine is shelved in favor of cocktails, and there’s already an empty six pack sitting on the coffee table. In this setting, the show takes on a friendly, yet honest tone that offers a refreshing respite to the army of Las Vegas journalists regurgitating the unending barrage of Las Vegas press releases. The unfiltered discussion centers around the latest Las Vegas news and happenings, and is supplemented with candid trip reports and storytelling that bring out the hosts’ likable personalities.

Beyond the hosts themselves, Tim and Michele have cultured a loyal following that is better described as a community rather than a listener base. Each episode includes a segment of voicemail calls that showcase the friendly, like-minded group with calls ranging from Las Vegas tips and reviews to drunken ramblings about awful hotel experiences. The podcast’s listeners are a good spirited group of fellow Las Vegas fanatics that follow the same “no B.S.” mantra held by FHBM’s hosts.

Beyond the voicemail segment, the listeners’ friendly atmosphere is on display on FHBM’s facebook group. It serves as a capable refuge for fellow the Las Vegas fanatics to indulge in the latest Las Vegas banter between episodes. In fact, the group won a Vegas Trippie award for Best Community after being retired from the podcast category following five consecutive wins. It might not be a Marconi Radio Award, but it still stands a testament that FHBM has evolved into something beyond a podcast.

Recently, Vegas Hotel Hunt had the opportunity to toss a few questions Tim’s way. Enjoy this interview with Tim Dressen, host of Five Hundy by Midnight – The Original Las Vegas Podcast.

VHH: First things first. What was the original inspiration to start Five Hundy by Midnight?

TD: When I first heard about podcasts and listened to a couple, I knew I wanted to give it a shot. As a kid, I had aspirations to be on the radio when I grew up. By the time I was old enough to pursue a career, radio was no longer appealing. With few exceptions, it had become homogenized and boring. So along comes podcasting—essentially DIY radio. That spark from my youth was rekindled. Deciding what type of show to do was easy. The one thing I can talk about endlessly is Las Vegas. It’s my favorite escape from reality, and it’s always changing. So Five Hundy by Midnight was born.

VHH: What keeps you going after over 350 episodes?

TD: First, Michele and I have a lot of fun recording it. Like Las Vegas, it’s a nice escape from anything stressful happening in our lives. Second, our listeners are amazing. They’re engaged, dedicated and extremely supportive of Five Hundy. The interaction and positive feedback from so many listeners helps keep us motivated to keep this thing alive.

VHH: Your lovely wife, Michele, is a great co-host on the podcast. Were you both into Las Vegas when you met, or did one of you have to convert the other?

TD: Neither of us had been to Las Vegas when we met. Our first trip occurred when we got married there. We weren’t immediately in love with the place but it grew on us. After a few trips, we were both hooked.

VHH: One of the things that makes Five Hundy by Midnight so refreshing is that you and Michele aren’t afraid to voice your opinion. Have you ever received any backlash or damage control from the hotels?

TD: I know that a bunch of hotel/casino employees listen, but I don’t hear from them very often. I get the feeling that most of them don’t really know what to do with those of us who freely give our opinions and don’t depend on them for ad income. For so long, the Las Vegas media has been the casino industry’s bitch. They’ll report on just about anything the casino companies’ PR machine cranks out without any sort of skepticism or tough questions. While we don’t purport to be covering Las Vegas as journalists, we do give our opinions. When something smells rotten, we point it out. That said, I have had a few heated e-mail exchanges with entertainers, authors and Las Vegas entrepreneurs whose projects we’ve ripped. Occasionally a listener or two will get really upset about something we’ve said too. I don’t aim to upset anyone, but because much of our show is opinion-based and off-the-cuff, it comes with the territory.

VHH: There’s clearly a healthy group of die-hard Las Vegas regulars, a good portion of which likely listen to your podcast. What do you think keeps people so interested in Vegas year after year?

TD: For one, Las Vegas is in constant flux. Even though there’s not a lot of new hotel construction happening these days, new shows, restaurants, bars, nightclubs and entertainment options spring up frequently. We visit three or four times a year, and we always have new things to try. Second, it’s hard to have a bad time in Las Vegas. Granted, it’s not for everyone. But if you visit and have a great time, it makes sense that you’d want to go back again (and again and again).

VHH: I love the voicemail line that you have for impromptu trip reports and general Vegas ramblings. It seems like a good percentage of these calls come in from listeners in a less than sober state. Do you have any unforgettable callers or messages? Anything so over the top it couldn’t hit the air?

TD: Ah yes… the voicemail line. I have a love/hate relation with that thing. I love the interaction it gives us with our listeners and the great information (and frequently entertainment) they provide. The part I hate is deciding which calls to use. I use about 75 percent of the messages. I feel somewhat obligated because people are taking the time and making the effort to share their experiences and be part of the show. Those that don’t make the cut typically fall into one of three categories: 1. Horrible sound quality. 2. Super long and rambling call with little useful information. (Lady, nobody cares that you had a good flight that left Toledo at 7:13 a.m., right on time!) 3. High frequency. If someone calls 10 times a month, I get a bit selective.

None of the calls were so over-the-top that I didn’t use them. I did, however, edit a handful of past shows to eliminate calls from a listener who was purporting to be a Las Vegas magician. It was obvious that it was a comedy bit and not the actual magician, but when the magician got wind of it, he wasn’t amused. He sent me a poorly written threat to sue if I didn’t remove the offending calls. I knew it didn’t have legal merit, but I didn’t need the headache. So I agreed to cut out those calls.

VHH: Vegas Podcast-a-Palooza was something you were part of for a few years. How did that all get started, and what ultimately caused its demise last year? It seems like this has evolved into the Vegas Internet Mafia Family Picnic. What can would-be attendees expect for that in October?

TD: Hunter Hillegas (from Vegas Gang) suggested the idea to Steve Friess (from The Strip) and me that it would be fun to have a live event with all three shows. All of us had individually met and become friends previously, so the chance to do something together seemed like it would be fun. When we started to talk about doing a fourth VPP, it sort of crumbled. Michele and I weren’t able to participate because of other travel plans and, quite honestly, because #3 was super stressful. Steve was winding down The Strip in anticipation of moving from Las Vegas. Fortunately, from the ashes of VPP, the Vegas Internet Mafia Family Picnic sprung like a phoenix. Last year’s event featured the Vegas Gang podcast live and a few activities with the crew from Vegas Tripping. This year, Five Hundy will be joining in. We’ll be doing a live show, much like we did at VPP. We’re super stoked to be part of VIMFP.

VHH: Besides media hype around unfunded projects and getting long-hauled from McCarran, what are your biggest Las Vegas pet peeves?

TD: Currently, my greatest irritation is the increasing number of Strip-side pests—people dressed up as cartoon and movie characters shilling for tips, timeshare salespeople, guys trying to get me to buy their shitty hip hop CDs and scammers trying to sell nightclub passes. Others include: groups of tourists who walk slowly, blocking the sidewalk; parents who bring their underage kids to Las Vegas; poor property maintenance by Caesars Entertainment; and the always decline state of video poker pay tables in Strip casinos.

VHH: It seems like you and Michele switch up the hotel choices for each trip. Generally the top hotels have nicer rooms and lower tier hotels have dated rooms. Do you know of any great exceptions, where a lower tier hotel has a particularly nice room or a top hotel has particularly poor accommodations?

TD: We get a ton of questions about which hotels are the greatest value and which are overpriced. We typically recommend Monte Carlo and Flamingo as the best bangs for the buck. The location of both is fantastic, the accommodations are clean (although some Flamingo room are a little rough around the edges) and the rate is typically lower than neighboring casinos of a similar quality. Caesars Palace and Planet Hollywood are among the worst values on the Strip. Although many of their room options are quite nice, they’re frequently priced in the same range as much higher quality hotels.

VHH: From time to time you bring on guest speakers to interview on Five Hundy by Midnight. Who was your favorite interview? Can you give us an episode number so we could check it out?

TD: Interviews are a relatively new addition to the show. I’ve only done a couple—Seth Schorr from Fifth Street Gaming, which is renovating the closed Lady Luck hotel (show #327), and Derek Stevens from Golden Gate and The D (shows #336 and #343). Both were really fun. I’m planning to do more interviews soon.

VHH: What is the story behind your side project, Is it just an online niche that were looking to fill, or do the bars hold a special place in your heart? Any can’t miss spots?

TD: In the past couple years, we’ve been enjoying the Downtown Las Vegas experience more and more. A big part of our relatively new-found love of downtown was the addition of the bars in the Fremont East entertainment district. When trying to find information about those bars about a year ago, I found that details were scarce and scattered. Some of the bars don’t even have their own websites. So I decided to develop a central location with details on all of the bars on and around Fremont Street. I continue to expand the site, adding new sections, reviews and anything else interesting related to the Fremont Street area.

Downtown Cocktail Room is one of our favorites, and we really enjoyed Mob Bar, which we recently visited for the first time.

VHH: Despite the affinity for video poker, you and Michele definitely know your way around the slot machine world, too. She even mentioned dreaming up new Spice Girls slot machines in episode #352. What are some of your favorite slot machines? What’s your preferred poison with table games?

TD: Goldfish is always entertaining, although I’ve rarely won anything. Recently, I’ve played Ghostbusters quite a bit too. I tend to migrate to the machines with familiar themes (TV shows and movies). I’m like a raccoon drawn to shiny objects—give me a fun bonus round with cool animation and I’m hooked. Playing these games isn’t the best gambling strategy, but they can be very entertaining.

I always intend to play more table games but rarely do. For a few years, I played a lot of pai gow poker. I had a craps phase too. I’ve played a little blackjack. I’ve tried three-card poker a few times. Because I tend to be fairly introverted, I’m not naturally drawn to table games as much as I am to machines.

VHH: Besides The Vegas Internet Mafia Family Picnic in October, when is your favorite time of the year to travel to Las Vegas?

TD: Our most frequent Las Vegas months are March and November.

VHH: Give us your best tip for a Las Vegas newbie, and a Las Vegas veteran.

TD: Newbie: Don’t pay retail for show tickets. Between the online discounters and the same-day ticket brokers, paying box office prices is rarely necessary (with a few headliner exceptions like Celine Dion and Garth Brooks).

Veteran: Don’t get too locked into a routine. It’s easy to fall into a rhythm in Las Vegas, staying at a favorite hotel and dining at favorite restaurants. Many of our best experiences have come from changing things up and trying new places.

Tim’s Vegas Picks:

  1. Overall Hotel: Cosmopolitan
  2. Show: Human Nature
  3. Attraction: Fountains at Bellagio
  4. Buffet: Wynn
  5. Bar: Strip: Book & Stage/Chandelier (tie); Downtown: Downtown Cocktail Room
  6. Pool: Cosmopolitan, I guess. We spend almost no time at the pool.
  7. Casino: I don’t really have a favorite right now.
  8. Biggest Win: two $4,000 royal flushes on the same machine in the same day at Venetian
  9. Best Comp Received: Corner suite at Aria + $1,000 gambling credit + $200 food credit + two Cirque tickets
  10. Best Vegas Memory: Marrying Michele (you know if I hadn’t said that, I’d be a dead man)
  11. Favorite Las Vegas Icon: Sinatra
  12. Hidden Gem: Mandarin Bar at Mandarin Oriental

Many thanks to Tim for entertaining the interview. For endless Five Hundy by Midnight goodness, check out the entire catalog of episodes over at

One Comment

  1. Really enjoyed the interview. While the “Meet The Gang” series had been done for the Vegas Gang podcasters of Chuck, Hunter, Dr. Dave, and Jeff Simpson (RIP), I don’t remember somebody doing something this in-depth on Hundy. It is always interesting to get into the heads of the mostly out-of-town “renegade” new media that covers the city. Outside perspectives are good.

    I won’t lie: Those of us in the PR/Copy-Paste/Advertising machine here in Las Vegas are utterly amazed knowing the incredible amount of time and effort that goes into prepping and producing a show of their caliber (not to mention, which I’ll shill because it is a great concept… wish we had thought of it). We know the hours and hours (and hours) it takes to pour through all the newspapers, RSS feeds, blogs, tweets, you name it. An impressive amount of work.

    And all for mostly a labor of love, knowing that they are shunning the possibility of good money in order to “keep it real”.

    Here’s to them inching toward the 500’th episode of Five Hundy.

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