He hit the country music scene nearly 10 years ago and has had a bunch of unforgettable hits in that short amount of time. Dierks officially began is country music career back in 2003 when he signed a record deal, and in that same year, he released his self titled debut album. He has even ventured into the bluegrass realm with his 2010 "Up on the Ridge" album. For someone fairly new to the world of country music, he has definitely made a big impact. Today, I'd like to share with you my Top 5 Favorite Dierks Bentley Songs.

  • 5

    "Free and Easy (Down the Road I Go)"

    This song is back from 2007, off of his "Long Trip Alone" album. It's a perfect song to play as you're driving down a country road in the summer--it has that kind of feel to the song. And, that's what I like about it. To quote the song, "Living life like a Sunday stroll."

  • 4

    "Lot of Leavin' Left To Do"

    Back from 2005, here's my number four favorite Dierks Bentley song--Lot of Leavin' Left to Do. From Wikipedia, "Deborah Evans Price, of Billboard magazine reviewed the song favorably, calling it a "personality packed uptempo number" "with the driving lead guitar and macho-lover lyric." She goes on to say that the song is "reminiscent of Waylon Jennings at his charismatic outlaw best."

  • 3

    "Rovin' Gambler"

    Here's a really good bluegrass song. This is one of my favorites from his "Up on the Ridge" album. I also featured this song on my "Country Stars with Bluegrass Crossovers" post. I mention that Dierks doesn't really have that traditional bluegrass voice (high-pitched and nasally), but his bluegrass venture is good nonetheless.

  • 2


    We just started playing this song on Big Frog 104 and it's great. It's catchy and fun to sing along to. This song is off of his album from this year "Home."

  • 1

    "What Was I Thinkin'"

    A classic back from 2003, here's my number one favorite Dierks Bentely song. It's just one of those great story songs. Definitely a fun song to sing along to.