Saddest Songs of 2009 / 2010

SmoothCriminal

The Top Ten

1 This is It - Michael Jackson This is It - Michael Jackson

Not the saddest if he had lived, but clearly the saddest once we consider the context...

it's sad cos, he didn't finish what he was born 4 - SmoothCriminal

2 When I Look at You - Miley Cyrus When I Look at You - Miley Cyrus

This played at my BFF's funeral - SmoothCriminal

I was the one that wrote this list and I had about 27 sad songs I choose the top ten now I can't choose so when this played my special friend died and this song played at her funeral - SmoothCriminal

When I first heard this song I almost teared up, it's still bothering me, maybe because I'm INLOVE with her - SmoothCriminal

This song is so sad x its also just an all round great song x

3 Baby - Justin Bieber Baby - Justin Bieber

WHAT HOW IS THIS SAD? he's saying "OOH BABI BABI OOH" over and over again, no meaning

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4 Already Gone - Kelly Clarkson Already Gone - Kelly Clarkson

I love her and this song just makes me weep :( crying is what I do listening to this song.

Already Gone is my favourite Kelly Clarkson song! She's AweSome!

5 Teaching Angels How to Fly - Jackie Evancho

Song about a tragic young lady, sung by a wonderfully empathic and talented young lady. - BobG

Composed by James Breedwell, this song is epic in the Beautiful Lyrics about a Child that is in heaven... Jackie Evancho is the only one to sing this song, or ever will be...

From her CD "Prelude To A Dream", about a young girl named Kimberly who died. A guaranteed weeper.

You may see Jackie re-record this presentation in the very near present.

6 Bad Romance - Lady Gaga Bad Romance - Lady Gaga V 1 Comment
7 New Divide - Linkin Park New Divide - Linkin Park

Linkin Park have a way with lyrics - this song is loaded with meaning.

It's sad to me because it reminds me of my crush

8 Meet Me Halfway - Black Eyed Peas Meet Me Halfway - Black Eyed Peas

What? Miley Cyrus is #1? Anyway, Meet Me Halfway is definitely the saddest song on this list.

9 Tears Don't Fall - Bullet for My Valentine Tears Don't Fall - Bullet for My Valentine
10 Wavin' Flag - K'naan Wavin' Flag - K'naan

K'naan made a legendary song and that would memorable because this little kid made his own song and attracted the hearts of all over the world

This should be at top it's a heart touching song

I loved it very much I often cry after hearing this

The Newcomers

? Try Sleeping with a Broken Heart - Alicia Keys Try Sleeping with a Broken Heart - Alicia Keys

very deep and touching track - Alexandr

? I Look to You - Whitney Houston I Look to You - Whitney Houston
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The Contenders

11 Superblind - Robbie Williams Superblind - Robbie Williams
12 Perfect - Hedley Perfect - Hedley
13 Written In My Face - Sean Jenness

It's a Really awesome song with a bad WWE Wrestler - SmoothCriminal

14 Concrete Angel - Jackie Evancho

From Jackie's 2009 "Prelude To A Dream" self-released album. Especially poignant hearing it sung with feeling and nuance by a nine-year-old.

15 Fiction - Avenged Sevenfold Fiction - Avenged Sevenfold
16 Alibi - 30 Seconds to Mars Alibi - 30 Seconds to Mars
17 You Found Me - The Fray You Found Me - The Fray
18 Last Kiss - Taylor Swift Last Kiss - Taylor Swift
19 So Far Away - Avenged Sevenfold So Far Away - Avenged Sevenfold

I found this song to be a great tribute to The Rev (their old drummer who died in 2009). If you listen to the song itself, it's not going to bring sadness. The music video was what brings in the tears.

20 Impossible - Toni Braxton
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List StatsUpdated 23 Feb 2017

500 votes
28 listings
6 years, 221 days old

Top Remixes

1. Baby - Justin Bieber
2. This is It - Michael Jackson
3. When I Look at You - Miley Cyrus
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