1. 55. Holiday
Holiday was the perfect island vibe from Hilary, but the song feels so forced by Hollywood Records pressuring her into releasing new work.
A+ to Hilary…F to Hollywood Records.
2. 54. Tell Me a Story (About The Night Before)
This holiday jam made every pre-teen want to get down on Christmas. Aside from the amazing feature of Lil’ Romeo, Hilary dominates turning hip hop into Christmas.
3. 53. Any Other Day
Any Other Day revealed a more mature, dark side to Hilary. It came from the time in her career where she was growing up and doing more independent work. The slow jam still makes your head bop and body sway.
4. 52. Burned
Burned might not of been one of the most memorable tracks from Dignity, but the way she tells the story is lyrically beautiful. The melody is perfect to go along with the lyrics, and Duff truly delivers on this outstanding track.
5. 51. Rock This World
Rock This World truly showed Hilary’s harder side, however it isn’t as memorable as her other rock anthems. No matter what, this song always makes me feel like a rebellious punk teen again.
6. 50. Cry
Cry is such a beautiful, heart-wrenching song with powerful lyrics. It will always hold a special place in Duff fans hearts, but isn’t remembered by the general public. (Which is obviously a shame.)
7. 49. The Math
There is no lie that The Math is an iconic song from her debut album. The lyrics are so perfectly 2003 – – this is *69.
(Side note- I definitely dressed up in a wig and dress to sing this at my 5th Grade talent show 11 years ago.)
8. 48. Between You and Me
This track is bubblegum pop to the core. It carries a Gwen Stefani sound with the maturity of Duff. This is the perfect move-on song to jam with the windows down in the summer.
9. 47. Love Just Is
If you were a tween or pre-teen in the Metamorphosis era, you definitely know that this was your first love song. It is so weird to think Hilary was only 15 when she recorded this beautiful track.
10. 46. Dangerous to Know
This song has Hilary Duff written all over it. From the lyrics, the hard rock chorus, and those belting vocals, this song was such a powerful track on her self-titled sophomore album.
11. 45. Never Stop
This song was basically written to us fans from Hilary (if you look at it like that.) Every time I am down, I blast this song to remember someone is always there. Hilary opens her heart in this track, and it has one of her best pop beats of all time.
12. 44. No Work, All Play
No Work, All Play is such an interesting track. It has the island vibe we love from Hilary, and the “lalala’s” are so freaking catchy. This is the classy “We Can’t Stop.” It is just as inspiring as it is fun.
13. 43. Shine
“Everyone knows that I’m 10 feet under.” Every time I hear that opening line I get so excited for whats to come. The chorus is just happy and fun.
14. 42. Underneath This Smile
Underneath This Smile is the original Ashlee Simpson. Hilary really opened up the world to this edgy side of pop music. This song just makes me want to hug her every time I hear it.
15. 41. Metamorphosis
Metamorphosis was an inside look to what Hilary was feeling around her big 16th. It was the most monumental event in the Metamorphosis era, and this title track was the icing on the cake.
16. 40. Hide Away
Hide Away made you want to crawl under your covers and cry. It is probably one of (if not the best) her best songs to just sit and cry to.
17. 39. Jericho
Jericho was such an uplifting, strange song. It really stood out on this album, and actually made you process what you were hearing.
18. 38. Supergirl
Supergirl. The title says it all.
19. 37. Haters
Dear Lindsay Lohan,
Take that, bitch!
Hilary Duff & Fans
20. 36. Danger
This was like Hilary’s big sister role to us. It was basically her way of telling us to use our eyes when it comes to dating. I now know to ask if you were born in 74. Thanks, Hil!
21. 35. I Am
I feel bad for kids today. I mean not having Hilary Duff to look up to in her prime? This is the most positive song she has ever released. If you ever feel down, simply look in the mirror and sing this.
22. 34. Play With Fire
Play With Fire might of been one of the most confusing moments in a Hilary Duff fans life. This was like nothing she had ever released before, and we immediately fell in love. Hilary is HOT in this video.
23. 33. Mr. James Dean
Just listen to the lyrics and the power in her voice. Simply put.
24. 32. Weird
This is personally one of my top 5 favorite Duff songs. The chorus is so freaking big and powerful. It sounds like a rock band at the Prom in a 1995 romantic comedy.
25. 31. I Wish
Preach. This song is deliciously direct and confident. Add this to the list of “SHOULDA BEEN A SINGLE.”
26. 30. Dreamer
Only Hilary can make a song with such a twisted background sound fun. It’s like I just want to laugh in that stalkers face and shout “BUM BUM BUM.”
27. 29. Break My Heart
This is my favorite of Hilary’s “harder” rock side. Singing it is like riding a roller coaster.
28. 28. Beat of My Heart
This song is in and of itself unique. It has the perfect mix of catchy, pop and classic rock Hilary while still maintaining this incredible fresh sound for her. Bravo, betch.
29. 27. Our Lips Are Sealed
Is there anything better than Hilary creating a better version of an already classic? Oh yeah…doing so with her kick-ass sister Haylie.
30. 26. Santa Claus Lane
All I Want For Christmas Is You? No, no. THIS is the best Christmas song. Ever.
31. 25. Sweet Sixteen
This song is weirdly personal. It just fits Hilary. I looked forward to singing this more on my 16th than getting my actual license.
32. 24. Who’s That Girl
A lot of the tracks on her sophomore album sound alike, including this one. This one however seems to be extremely personal and real. I just feel her pain, ya know?
33. 23. Outside of You
This has every ingredient to be a hit. It is catchy, fun and relatable. Another “SHOULDA BEEN A SINGLE.”
34. 22. Party Up
Before twerking and Molly…Hilary made partying cool and responsible. This was the ultimate “twerk” song for tweens, teens and all alike. COME ON AND LIGHT ME UP.
35. 21. Stranger
This is one of the most mature and unique sounds off Dignity. It not only captures a different sound, but the personal affiliation with her parents divorce makes you want to crawl into the video and punch the douche bag. No one hurts, Hil.
36. 20. Where Did I Go Right
I remember listening to this on repeat on my walkman back in the day. It’s just too…perfect. Wedding song, anyone?
37. 19. So Yesterday
This is such a sensitive subject for true Duff fans. We all know it wasn’t her first single, which is why we get so annoyed when people attribute it to her breakout. (I’m sorry but I Can’t Wait & Why Not count. Don’t get me started on What Dreams Are Made Of.) Although a fan favorite, this isn’t the song she should encore to.
38. 18. Do You Want Me
This is personally my second favorite Duff song. It is such a perfect hot mess. She sounds so edgy and punk, but still sweet old Hilary. It goes from pop to rock in a hot second. It’s just…perfect.
39. 17. What Dreams Are Made Of (Hey Now)
When you’re an icon, quality doesn’t measure as high as memories. This song is so important to her career, and it is catchy as hell. Goodbye, Lizzie. Hello, Hilary! *Tears*
40. 16. I Can’t Wait
This was the kick-start to her music career. This was the original Hannah Montana. Please, grab a box of kleenex and watch the video. I’m already crying.
41. 15. Dignity
This was like the sequel to “Haters.” It really redefined Hilary’s image and reminded America why we love her. Again, big sis Hil teaching us a lesson.
42. 14. Workin’ It Out
This song is just fun. It is young Hilary empowering the world, not to mention one of the best songs from Metamorphosis. “So cooool, that’s awesome!”
43. 13. Reach Out
Holy sh*t she grew up! Putting my anger towards Hollywood Records aside, this song is so sexy and fun. It was a major club hit and gave fans what they craved for years–a sexy Hilary Duff!
44. 12. Happy
This is the biggest “SHOULDA BEEN A SINGLE” song she released. It is such a powerful pop song and deserved to be on top.
45. 11. Gypsy Woman
Although never 100% confirmed, this song was rumored to be about her Father and the divorce. The beat is INCREDIBLE, and the lyrics hold so much power and passion. “Stumble Sta Sta Sta Stumblin”
46. 10. Why Not
I love that Hilary knows the importance of this song in her career. She sang it on every tour she went on and never forgot about it. Not only is it so freaking inspiring and catchy, it will hold the hearts of Duff fans forever.
47. 9. Fly
This song was hugely important for Hilary because it was the debut single after the extremely successful Metamorphosis. If you ever feel defeated, sing this. No, shout this.
48. 8. Girl Can Rock
I’m sorry…but this song is just killer. I know it…you know it…Hilary knows it. I mean come on, THE GIRL CAN ROCK.
49. 7. With Love
This is one of Hilary’s most successful singles. It is catchy, fun and the perfect dance song. Plus it brings back the black wig we love so much!
50. 6. The Getaway
This is one of Hilary’s favorite songs. It is so powerful and personal. I dare you to sing it full blast on the highway-absolute perfection.
51. 5. Anywhere But Here
This is the most free sounding song she’s released. You feel
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