I'll list all my favorites and then try to narrow down to a top 10. (This may take a few days and I'll be adding more to this list as I look through my collection.)
Jessica Andrews' "Helplessly, Hopelessly"
Beautiful video, love the scenery and Jessica was gorgeous in this one.
Steve Azar's "I Don't Have To Be Me ('Til Monday)" & "Waitin' On Joe"
Two very different moods but both were really great videos, I don't know why he wasn't a superstar.
Jeff Bates' "One Second Chance"
It may not be the most original video but it's really well done and captures the song perfectly.
Dierks Bentley's "What Was I Thinkin'", "Settle For A Slowdown", "Long Trip Alone", "Draw Me A Map", & "Bourbon In Kentucky"
All excellent and I honestly never realized how strong his videography is.
Big & Rich's "Save A Horse (Ride A Cowboy)"
Sure it may be nothing deep or anything but like the song it's exploding with energy and just goofiness. Also like Sarah Darling's part.
Catherine Britt's "The Upside Of Being Down"
Simple but I really like this one, not even sure why this stands out so much in my head.
Lisa Brokop's "Hey, Do You Know Me"
This one was out at a time where I would watch a ton of music videos on CMT and the canadian channel played this a lot.
Garth Brooks' "The Thunder Rolls"
I remember being scared by this as a kid, but it's a really great music video, it's too bad we don't see this that often anymore.
Brooks & Dunn's "You Can't Take The Honky Tonk Out Of The Girl" & "Believe"
Again completly different moods but I think the effort put into both really showed in the final product.
Sarah Buxton's "Outside My Window"
Fun, Colorful and just joyful. The fact that it was done so cheaply but is still more memorable than some really expensive ones shows just how creative the people behind this were.
George Canyon's "My Name"
I love that George and his label didn't shy away from the story of the song, this is a really underrated video I think.
Deana Carter's "There's No Limit"
Sure it's mostly memorable for Deana strutting around in her underwear but it's played down but still uses it's sexuality very nicely.
Marcel's "Tennessee"
Very beautiful song and video, there's a 2nd version of the video that Marcel filmed himself that's equally as great!
Kasey Chambers' "Like A River"
I remember discovering this song on CMT's website and falling in love with her voice, listening to her albums later on I grew to appreciate how this video captures her quirkyness.
Eric Church's "Lightning"
Great song, great video. Nothing more is needed to be said.
Terri Clark's "No Fear"
Such a beautiful and touching tribute to the Canadian Special Olympics.
Terri Clark's "Girls Lie Too", "Three Mississippi", "The World Needs A Drink",& "She Didn't Have Time"
Love Terri but these would be strong videos even without my love of her. "She Didn't Have Time" in particular was very cool in it's concept.
Kellie Coffey's "I Would Die For That"
I'm really hoping somebody one day will take this song and make it a big hit, but I doubt anybody will be able to top the video Kellie did.
Coldwater Jane's "Marionette"
I love when videos try something different and they really went for it on this one. This one is a definate stand out.
Elizabeth Cook's "Stupid Things"
Nice, Bright and cheery sometimes that done really well makes for a good video.
Bobbie Cryner's "You'd Think He'd Know Me Better"
Great song and while the video isn't my favorite (spoiler for top 10), I really do love it. (ps. listen to this song and tell me the twist at the end isn't greatness.
)
Cross Canadian Ragweed's "Fightin' For" & "Sick & Tired"
"Fightin' For" is stronger in concept and overall presentation, but seeing Lee Ann Womack in "Sick & Tired" was a great treat.
Chris Cummings' "Lucy Got Lucky"
Nothing amazing but it recalls the 1980's movies for me and I really enjoyed that.
Billy Currington's "Walk A Little Straighter"
I commended George Canyon's video for not shying away but this is a way to shy a way a little but still represent the story very well.
Amy Dalley's "Men Don't Change"
Fun, like I said sometimes that's more than enough to make something great.
Diamond Rio's "I Believe"
I remember being 13 years old when I first seen this and trying so hard not to cry, I miss videos like this.
Dixie Chicks' "Goodbye Earl", "Long Time Gone", "Top Of The World" & "Not Ready To Make Nice"
They really had strong videos and I really can't pick one of these to be my favorite of theirs.
Amber Dotson's "I'll Try Anything"
This is another I can't place why I love it like I do but something at the time it was out really connected me to it.
The Duhks' "Mists Of Down Below"
I love the mood and visuals of this video so so much. They really had a unique look to them as a group.
Kathleen Edwards' "Back To Me", "In State" & "The Cheapest Key"
After meeting her I love how much "The Cheapest Key" really captures her attitude but "Back To Me" is the best shot. "In State" though takes the cake as her best video because it's got a strong concept, it caputres her pretty well and it's got an interesting look.
Eli Young Band's "When It Rains"
They've never really gotten to the feel of this video again but I remember the look of it is what drew me into it and I had to find out more about the artist.
Emerson Drive's "Last One Standing"
It's a simple video but I really like the colors and it was I think a good representation of the band at the time.
Sara Evans' "Cryin' Game", "No Place That Far", "Born To Fly", "Perfect", "Suds In The Bucket", "A Real Fine Place To Start", "Cheatin'", "As If", "Low", "A Little Bit Stronger" & "Slow Me Down" are all great videos and honestly I think Sara may have my favorite collection of videos.
Shelly Fairchild's "You Don't Lie Here Anymore" & "Tiny Town"
Love them both, I especially love the direction of both. "You Don't Lie Here Anymore" was the first video from Kristin Barlowe that I remember seeing and "Tiny Town" was my first Trey Fanjoy. They're my two favorite directors so Shelly had great taste.
Jennifer Hanson's "'73 (Everything Changes)"
Simple but so touching getting to see the song play out in pictures from the artists life. I can't think of many videos that show the actual singers life. At least not off the top of my head.
Susan Haynes' "Drinkin' In My Sunday Dress"
I love watching this one as I am a sucker for single shot videos.
Eric Heatherly's "Flowers On The Wall", "Swimming In Champagne" & "The Last Man Committed"
Love all 3 of his videos. The weirdness of Flowers was so fun back in the day.
Faith Hill's "I Can't Do That Anymore", "This Kiss", "The Secret Of Life", "The Way You Love Me", "Cry", "Like We Never Loved At All" & "Stealing Kisses" were all really strong videos. I especially love "The Secret Of Life", sometihng about the way it's shot just makes it pop in my mind when I think about music videos.
Rebecca Lynn Howard's "No One'll Ever Love Me" & "That's Why I Hate Pontiacs"
Two very strong videos. One I like the story the other I like for the colors.
Jedd Hughes' "High Lonesome"
I love this video because it makes me want to travel the world to see new places.
Alan Jackson's "Midnight In Montgomery", "Chattahoochee", "Drive (For Daddy Gene)", "It's Five O'Clock Somewhere", "Remember When", "The Talkin' Song Repair Blue", & "Like Red On A Rose". Love them all, I love how effortless Alan appears in them all, really captures his personality I think.
I'll continue this in the future I'm getting tired of typing lol