Valley Personalities

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It's 4:45 on a Saturday, the regular crowd shuffles in…

For four decades, that lyric has been more than a Billy Joel song in Vail. It's been a ritual. Anytime Phil Long sang "Piano Man," he'd shout out to the crowd to ask what time it was and adjust the lyrics to fit the moment. The crowd always knew the answer. They'd been shuffling in — ski boots still on, cheeks still flushed from the mountain — to hear Phil Long do his thing.

Now, after 40 years of that beautiful, boot-stomping routine, the curtain is coming down. The legendary après ski entertainer will play his last show at Vail Chophouse in Lionshead on July 4. Fireworks and a finale — fittingly dramatic for a man who never once did things halfway.

From Broomfield to Bridge Street

Long, a native of Broomfield, Colorado, came to play music in Vail in 1987. "I told my parents when I graduated from college that I just wanted to try music. And my dad said, 'OK, well, make sure you have your health insurance,'" Long said.

Dad's advice was sensible. What happened next was something else entirely.

Phil Long started playing music at the Red Lion in the heart of Vail Village during the 1987–88 ski season. The Red Lion — that legendary ski bar that had been slinging drinks since Vail Mountain's very first season in 1963 — became Phil's living room, his stage, and eventually his business.

Name Dropping at 8150 feet

As a mainstay of Vail's social scene for four decades, the famous found their way to Phil’s stage. Long got to play at President Gerald R. Ford's house for New Year's Eve, and Bill Gates — an avid tennis player who knew Long was a former collegiate tennis player — once asked him to set up a match after attending one of Long's après ski sets.

Then there was the Gloria Estefan moment. "Just last year there was a huge group sitting in front of the stage and I thought, 'That looks sort of like Gloria Estefan.' Next thing you know, she's on stage singing with me and her 11-year-old grandson and we are singing 'Desperado,'" he said.

The Vail Valley Insider played a season of local rec league basketball with Phil and he had a jump shot that was nearly as consistent as his musical act!

The Lionshead Gamble

In 2015, Phil made his boldest business move yet, purchasing the Vail Chophouse in Lionshead. Moving the après ski party away from the familiar gravitational pull of Bridge Street was a genuine risk. "Lionshead was tricky. People were so used to the Bridge Street shuffle. To get them to come down to Lionshead we were like, 'C'mon, give it a try, it's OK over here,'" Long said. "And I feel proud that it went from literally having 10 people in there to having full reservations overflowing for shows."

Going Out on Top

Long announced his retirement in a social media post, writing: "I, with great emotion, health, happiness, support of my beautiful wife Vivian and family, am announcing my retirement from entertaining effective July 4, 2026. 40 years of entertaining seems a perfect crescendo AND with 19 great shows left!!"

The reasoning is as Phil Long as Phil Long gets. "I always wanted to go out on top. I never wanted someone to look on that stage and go, 'Oh, my gosh. Bless his heart. Is that what he's still doing?'" he said. "I still love to perform, I love the people, but I haven't had a New Year's Eve off since I was 18 years old."

"Whatever my little combination of being a decent player and being a good entertainer and working as hard as I can, it all paid off in ways that I never could have imagined," Long said. "I'm happy to end on a high note."

Vail won't be the same at 4:45 on a Saturday. But for everyone who shuffled in, boots still on, cold drink in hand, and sang their hearts out — those memories are permanent. Phil Long didn't just play music. He played Vail.

Phil Long's final show is July 4 at the Vail Chophouse in Lionshead.

From Vaildaily.com