This was just off the top of my head. I could go on and on. Just personal favorites of mine and not really in any order except for the first few. I could make a top 200 list and it'd be easier.
Agree completely - pulling together 50 was hard, particularly limiting it to 1 or 2 songs per artist. I did pretty well except for Brad Paisley (given his duets), I had to go w/ three of his.
1. You Had To Be There – Tim McGraw
2. Every Mile A Memory – Dierks Bentley
3. Right Where I Need To Be- Gary Allan
4. When I Get Where I'm Going - Brad Paisley & Dolly Parton
5. How Do You Like Me Now?- Toby Keith
6. Where Were You (When The World Stopped Turning)- Alan Jackson
7. Til The Last Shot’s Fired – Trace Adkins
8. Picking Wildflowers – Keith Anderson
9. It Just Comes Natural – George Strait
10. This is Country Music – Brad Paisley
11. Keep On – Eric Church
12. Fly Over States- Jason Aldean
13. Guilty As Can Be – Cody Johnson
14. Saturday Night – Wade Bowen
15. My Texas – Josh Abbott Band and Pat Green
16. Hard Candy Christmas – Dolly Parton
17. No Shirt, No Shoes, No Problem - Kenny Chesney
18. These Days- Glenn Campbell
19. Life Ain't Always Beautiful – Gary Allan
20. Tequila Makes Her Clothes Fall Off – Joe Nichols
21. Playboys of the Southwestern World – Blake Shelton
22. Where the Stars and Stripes and Eagles Fly – Aaron Tippin
23. Suspicious Minds - Elvis Presley
24. Everywhere Man- Johnny Cash
25. I Like It, I Love It – Tim McGraw
26. Should've Been A Cowboy- Toby Keith
27. If You’re Going Through Hell – Rodney Atkins
28. The Little Girl- John Michael Montgomery
29. Living for the Night- George Strait
30. Family Tradition- Hank JR.
31. I Just Came Back From A War – Darryl Worley
32. Too Country – Brad Paisley and Buck Owen
33. Getting You Home – Chris Young
34. South Carolina Low Country – Josh Turner
35. 5150 – Dierks Bentley
36. I’ll Sing About Mine – Josh Abbott Band
37. Find Out Who Your Friends Are - Tracy Lawrence, Kenny Chesney and Tim McGraw
38. Between Raising Hell and Amazing Grace- Big and Rich
39. You're Still The One- Shania Twain
40. Crazy – Patsy Cline
41. All of Me – Willie Nelson
42. Forever And Ever, Amen - Randy Travis
43. She Don’t Know She’s Beautiful – Sammy Kershaw
44. Crazy – Kenny Rogers
45. The Dollar- Jamey Johnson
46. I Love A Rainy Night – Eddie Rabbit
47. Granddaddy's Gun- Aaron Lewis
48. My Town - Montgomery Gentry
49. The House That Built Me-Miranda Lambert
50. The Devil Went Down To Georgia – Charlie Daniels Band