Top 20 Cowboy Songs in the Past 20 Years

We gave cowboy music radio host Charley Engel the daunting task of choosing the Top 20 core cowboy songs of the last 20 years, and he didn''t disappoint. Here they are!
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We gave cowboy music radio host Charley Engel the daunting task of choosing the Top 20 core cowboy songs of the last 20 years, and he didn''t disappoint. Here they are!
ridersinthesky

Creating a Top 20 list was a task for Solomon himself. To do so, I had to set some exacting criteria:

1) Only one listing per artist

2) The song had to be written or co-written by the artist (with a few exceptions)

3) The track had to be released by that artist for the first time during that year.

Hopefully, you will remember some old favorites and discover a few new gems.

Note: To hear a special show featuring these songs, log on to Engel's show on The Flying SL Ranch Radio at https://radio.spalding-labs.com

1994

"Born To Be A Cowboy"—R.W. Hampton

(Born To Be A Cowboy)

One mark of success is how many times your song has been covered. There are no less than nine versions by other top artists.

Editor’s pick: No Ordinary Man—Tracy Bird (No Ordinary Man)

1995

"Riding The Winds Of The West"—Riders In The Sky

(Always Drink Upstream From The Herd)

Not only is Ranger Doug the “Idol of American Youth,” but he can pen a western tune to rival Bob Nolan.

Editor’s pick: The Beaches Of Cheyenne—Garth Brooks (Fresh Horses)

1996

"The Habit"—Don Edwards

(West Of Yesterday)

Edwards mostly records classic songs from by-gone days except for this poem by Berton Braley that Don expanded and adapted to music. Pure Don!

Editor’s pick: That’s Right (You’re Not from Texas)—Lyle Lovett (Road to Ensenada)

1997

"The Sky Above the Mud Below"—Tom Russell

(Song Of The West)

A dark tale of two long-haired Mexican braiders-turned-horse thieves that are forced to weave their nooses out of their own hair.

1998

"Wolves"—Stephanie Davis

(River of No Return)

Garth Brooks made it famous, but here is the composer’s version, and the song that really launched her performing career.

1999

"Ridin’ Easy With The Sun"—Sons Of San Joaquin

(Horses Cattle & Coyotes)

Jack Hannah has become one of the finest writers of western music, and this track is just one example of his fine skill.

2000

"Cowboy True"—“Curly” Jim Musgrave

(Cowboy True)

A splendid telling of the multi-ethnic make up of the old-time drovers. Not bad for a Canadian-born therapist and counselor. He will be missed!

2001

"Patrick"—Mike Beck

(Mariposa Wind)

The story of a horse owned and trained by Bill Dorrance, one of the fathers of “Natural Horsemanship.” Simple, haunting, and memorable.

Editor’s pick: The Cowboy In Me—Tim McGraw (Set This Circus Down)

2002

"We Danced on the Oregon Trail"—Red Steagall

(Wagon Tracks)

Steagall holds the title of “The Official Cowboy Poet of Texas” for good reason. He’s a master at spinnin’ a good tale set to music.

2003

"Rodeo Moon"—Chris LeDoux

(Horsepower)

A co-write with Toby Keith, this ditty presents the eternal optimism coursing through the veins of every competitor who’s ever entered the arena to win.

Editor’s pick: Cowboys Like Us—George Strait (Honkytonkville)

2004

"Cowboy Up"—Joni Harms

(Let’s Put The Western Back In The Country)

Joni has long championed western music in a genre dominated by Nashville execs that are “all hat and no cattle.” One of her best!

2005

"This is My Sky"—Ian Tyson

(Songs from the Gravel Road)

Pick his “best” from 20 years? No way! Tyson’s writing is so unlike any of his peers that he holds a unique place among many great talents.

2006

"Silver Music"—Juni Fisher

(Cowgirlography)

Prior to becoming a professional entertainer, Juni trained cow horses and cutters. She and her mount dance to “silver music” as played by the horse’s bit.

2007

"If I Hadn’t Seen the West"—Joyce Woodson

(If I Hadn’t Seen the West)

Woodson really hit her stride with her third release. It was an instant classic and a must-own for any fan of pure western music.

2008

"Where Horses Are Heroes"—Wylie & The Wild West

(Bucking Horse Moon)

Wylie’s western songs are written with the authority that comes from one who lives the life. A paean to cow ponies.

Editor’s pick: Cowgirls Don’t Cry—Brooks & Dunn (Cowboy Town)

2009

"Come Ride With Me"—Dave Stamey

(Come Ride With Me)

A frustrated novelist, Stamey aims to reach more people with a three-minute song than a lengthy book. Saddle up and join him on the trail!

2010

"Monster On Your Back"—Brenn Hill

(Equine)

Loud guitars and a pounding beat shake the dust off of western music for a whole new audience while remainin’ true to it’s roots. This thing kicks ass!

2011

"Partner To The Wind"—Michael Martin Murphey

(Tall Grass & Cool Water—Cowboy Songs VI * Buckaroo Blue Grass III)

Murph does it again! After 41 years of hits, he’s still at the top of his game.

2012

"Ride Cowboy Ride"—Terry Brown

(It’s A Cowboy Thang)

Old title—new song. Brown whips this one over and under to take us on a wild, runaway gallop across a wide-open prairie. Ye-haw, pard!

2013

"Jealous Of The Moon"—Mary Kaye

(The Dawn And The Dusk)

A. How does a mother of 10 still look so gorgeous? B. Where’d she get pipes like that? Be prepared to be blown away. ¡Muy bueno!

2014

Remains to be seen!

To hear a special show featuring these songs, log on to Engel's show on The Flying SL Ranch Radio at https://radio.spalding-labs.com