1 “50 Ways to Leave Your Lover” – Paul Simon
2 “Absolutely Zero” – Jason Mraz
3 “Against All Odds” – Phil Collins or The Postal Service version
4 “All Alone Am I” – Brenda Lee
5 “All By Myself” – Eric Carmen (definitely not the Celine Dion version; the Bridget Jones version works, but only with the visual)
6 “All My Ex’s Live in Texas” – George Strait
7 “Alone Again (Naturally)” – Gilbert O’Sullivan
8 “Another Lonely Day” – Ben Harper
9 “Apart” – The Cure
10 “Are You Lonesome Tonight” – Elvis Presley
2 “Absolutely Zero” – Jason Mraz
3 “Against All Odds” – Phil Collins or The Postal Service version
4 “All Alone Am I” – Brenda Lee
5 “All By Myself” – Eric Carmen (definitely not the Celine Dion version; the Bridget Jones version works, but only with the visual)
6 “All My Ex’s Live in Texas” – George Strait
7 “Alone Again (Naturally)” – Gilbert O’Sullivan
8 “Another Lonely Day” – Ben Harper
9 “Apart” – The Cure
10 “Are You Lonesome Tonight” – Elvis Presley
11 “Ballad of Big Nothing” – Elliott Smith
12 “Black” – Pearl Jam
13 “Blackout” – Muse
14 “Blue Moon Revisited” – Cowboy Junkies
15 “Can’t Stand Losing You” – The Police
16 “Careless Whisper” – Wham!
17 “Crazy” – Patsy Cline or Willie Nelson
18 “Crown of Love” – Arcade Fire
19 “Crying” – Roy Orbison
20 “Don’t Cry Out Loud” – Melissa Manchester
21 “Don’t Leave Me This Way” – Thelma Houston
22 “Don’t Walk Away” – ELO
23 “Don’t You Want Me” – The Human League
24 “Ever Fallen in Love” – The Buzzcocks
25 “Every Breath You Take” – The Police
26 “Everybody Hurts” – R.E.M.
27 “Everyday I Love You Less and Less” – Kaiser Chiefs
28 “Ex-Factor” – Lauren Hill
29 “Ex-Girlfriend” – No Doubt
30 “Girl from the North Country” – Bob Dylan
31 “Girl” – Beatles
32 “Grace Cathedral Hill” – The Decemberists
33 “Harden My Heart” – QuarterFlash
34 “Heartbreak Hotel” – Elvis Presley
35 “Heartbreaker” – Pat Benatar
36 “Hopelessly Devoted to You” – Olivia Newton John (Grease Soundtrack)
37 “How Can You Be Sure?” – Radiohead
38 “I Fall to Pieces” – Patsy Cline
39 “I Hope You’re Happy Now” – Elvis Costello
40 “I Never Cared for You” – Willie Nelson
41 “I Used to Love Her” – Guns n’ Roses
42 “I Want You” – Elvis Costello
43 “I Will Survive” – Gloria Gaynor
44 “If I Can’t Have You” – Yvonne Ellimen
45 “I’m So Lonesome I Could Cry” – Take your pick: Hank Williams, Elvis Presley, Cowboy Junkies, or Johnny Cash
46 “I’m Sorry” – Brenda Lee
47 “It’s a Heartache” – Juice Newton or Bonnie Tyler
48 “It’s Not Right, But It’s Okay” – Whitney Houston (the Thunderpuss remix)
49 “It’s Over” – Roy Orbison
50 “I’ve Been Loving You Too Long” – Otis Redding
51 “Killing Me Softly with His Song” – Fugees over Roberta Flack
52 “Last Goodbye” – Jeff Buckley
53 “Leavin’ on Your Mind” – Patsy Cline
54 “Lilac Wine” – Jeff Buckley
55 “Lonesome Tears” – Beck
56 “Lost Cause” – Beck
57 “Love Hurts” – Nazareth (the cover by Joan Jett will do in a pinch)
58 “Love is Stronger Than Death” – The The
59 “Love on the Rocks” – Neil Diamond
60 “Love Stinks” – J. Geils Band
61 “Love Will Tear Us Apart” – Joy Division
62 “Lover, You Should Have Come Over” – Jeff Buckley
63 “Lush Life” – Billy Strayhorn
64 “Mandy” – Barry Manilow
65 “No More Tears (Enough Is Enough)” – Barbra Streisand & Donna Summer
66 “Nothing Compares to You” – Sinead O’Connor or Prince
67 “One” – Aimee Mann (Magnolia soundtrack)
68 “Ordinary World” – Duran Duran
69 “Run” – Snow Patrol
70 “Separate Ways” – Journey
71 “She Is Gone” – Willie Nelson
72 “She’s Got You” – Patsy Cline
73 “Should’ve Been in Love” – Wilco
74 “Since I Don’t Have You” – Guns N’ Roses version
75 “Since U Been Gone” – Kelly Clarkson
76 “So Lonely” – The Police
77 “So Wrong” – Patsy Cline
78 “Soma” – Smashing Pumpkins
79 “Somebody That I Used to Know” – Elliott Smith
80 “Strange” – Patsy Cline
81 “Sweet Dreams” – Patsy Cline
82 “Tainted Love” – Soft Cell
83 “The Seventh Stranger” – Duran Duran
84 “The Sign” – Ace of Base
85 “There’s a Tear in My Beer” – Hank Williams
86 “These Arms of Mine” – Otis Redding
87 “This Woman’s Work” – Kate Bush
88 “Total Eclipse of the Heart” – Bonnie Tyler
89 “True Happiness This Way Lies” – The The
90 “Two Out of Three Ain’t Bad” – Meatloaf
91 “We Belong ” – Pat Benatar
92 “Why Can’t He Be You” – Patsy Cline
93 “Without You” – Henry Nilsson (not the Mariah Carey version)
94 “Writing to Reach You” – Travis
95 “You Give Love a Bad Name” – Bon Jovi
96 “You Oughta Know” – Alanis Morissette
97 “You’ll Never Find Another Love Like Mine” – Lou Rawls
98 “Your Ex-Lover is Dead” – Stars
99 “You’re Not the Girl You Think You Are” – Crowded House
100 “You’ve Lost That Loving Feeling” – Righteous Brothers