1 Bing Crosby White Christmas 1942
2 Bill Haley & His Comets Rock Around the Clock 1955
3 Judy Garland Over the Rainbow 1939
4 Bryan Adams (Everything I Do) I Do it For You 1991
5 The Beatles Hey Jude 1968
6 Celine Dion My Heart Will Go On 1998
7 Leona Lewis Bleeding Love 2008
8 Whitney Houston I Will Always Love You 1992
9 Glenn Miller In the Mood 1940
10 Abba Dancing Queen 1976
11 The Beatles She Loves You 1963
12 Shakira & Wyclef Jean Hips don't lie 2006
13 Pink Floyd Another Brick in the Wall (part 2) 1980
14 Sinead O'Connor Nothing Compares 2 U 1990
15 Bobby Darin Mack the Knife 1959
16 George Harrison My Sweet Lord 1971
17 Fred Astaire The Way You Look Tonight 1936
18 Cher Believe 1998
19 John Lennon Imagine 1971
20 Elvis Presley Jailhouse Rock 1957
21 The Beatles I Want to Hold Your Hand 1964
22 Coolio Gangsta's Paradise 1995
23 Queen Bohemian Rhapsody 1976
24 The Beatles Let it Be 1970
25 John Travolta & Olivia Newton-John You're the One That I Want 1978
26 Usher Yeah! 2004
27 Kylie Minogue Can't Get You Out of My Head 2001
28 USA For Africa We Are the World 1985
29 The Village People YMCA 1978
30 Bing Crosby Pennies From Heaven 1936
31 Britney Spears Baby One More Time 1999
32 Nat King Cole Mona Lisa 1950
33 Al Jolson Swanee 1920
34 Stevie Wonder I Just Called to Say I Love You 1984
35 Spice Girls Wannabe 1996
36 Bing Crosby Swinging On a Star 1944
37 Terry Jacks Seasons in the Sun 1974
38 Ben E King Stand By Me 1961
39 Roy Orbison Oh, Pretty Woman 1964
40 Procol Harum A Whiter Shade of Pale 1967
41 Carl Douglas Kung Fu Fighting 1974
42 P Diddy & Faith Evans I'll Be Missing You 1997
43 Bee Gees Stayin' Alive 1978
44 Madonna Like a Prayer 1989
45 Elvis Presley Are You Lonesome Tonight? 1960
46 Kim Carnes Bette Davis Eyes 1981
47 Don McLean American Pie 1972
48 Lou Bega Mambo No 5 (A Little Bit of ...) 1999
49 Eminem Lose Yourself 2002
50 Irene Cara Flashdance... What a Feeling 1983
1 Bing Crosby White Christmas 1942
2 Bill Haley & His Comets Rock Around the Clock 1955
3 Judy Garland Over the Rainbow 1939
4 Bryan Adams (Everything I Do) I Do it For You 1991
5 The Beatles Hey Jude 1968
6 Celine Dion My Heart Will Go On 1998 7 Leona Lewis Bleeding Love 2008
8 Whitney Houston I Will Always Love You 1992
9 Glenn Miller In the Mood 1940
10 Abba Dancing Queen 1976
11 The Beatles She Loves You 1963
12 Shakira & Wyclef Jean Hips don't lie 2006
13 Pink Floyd Another Brick in the Wall (part 2) 1980
14 Sinead O'Connor Nothing Compares 2 U 1990
15 Bobby Darin Mack the Knife 1959
16 George Harrison My Sweet Lord 1971
17 Fred Astaire The Way You Look Tonight 1936
18 Cher Believe 1998
19 John Lennon Imagine 1971
20 Elvis Presley Jailhouse Rock 1957
21 The Beatles I Want to Hold Your Hand 1964
22 Coolio Gangsta's Paradise 1995
23 Queen Bohemian Rhapsody 1976
24 The Beatles Let it Be 1970
25 John Travolta & Olivia Newton-John You're the One That I Want 1978
26 Usher Yeah! 2004
27 Kylie Minogue Can't Get You Out of My Head 2001
28 USA For Africa We Are the World 1985
29 The Village People YMCA 1978
30 Bing Crosby Pennies From Heaven 1936
31 Britney Spears Baby One More Time 1999
32 Nat King Cole Mona Lisa 1950
33 Al Jolson Swanee 1920
34 Stevie Wonder I Just Called to Say I Love You 1984
35 Spice Girls Wannabe 1996
36 Bing Crosby Swinging On a Star 1944
37 Terry Jacks Seasons in the Sun 1974
38 Ben E King Stand By Me 1961
39 Roy Orbison Oh, Pretty Woman 1964
40 Procol Harum A Whiter Shade of Pale 1967
41 Carl Douglas Kung Fu Fighting 1974
42 P Diddy & Faith Evans I'll Be Missing You 1997
43 Bee Gees Stayin' Alive 1978
44 Madonna Like a Prayer 1989
45 Elvis Presley Are You Lonesome Tonight? 1960
46 Kim Carnes Bette Davis Eyes 1981
47 Don McLean American Pie 1972
48 Lou Bega Mambo No 5 (A Little Bit of ...) 1999
49 Eminem Lose Yourself 2002
50 Irene Cara Flashdance... What a Feeling 1983
Leona better demolish the other girls. The only song from the 21st century up there.
I was in middle school when Taylor Swift made her big break on her first album. This was 2007/2008 time. Teardrops On My Guitar was the first song I heard from her too, and I really liked it. Then I heard Our Song and liked that too.
My friends were all obsessed with her around that time and gave me a copy of her 1st CD. Then I got Fearless from them too.
I didn't start buying her CDs on my own until Speak Now ,and I have been slacking on getting the Platinum Edition of Fearless but I will get on that eventually lol.