I knew enough songs in 2005 to map out most of that year... even if I wasn't following chart music at all before sometime in November of that year. It was just in time for all the year-end retrospective stuff so.. :P
Anything before 2005 is just whatever I heard on the radio or from those around me (though I was pretty removed from pop music in 2003/2004.. but I wasn't missing out on much in those years). I can't really map out these years well enough into weekly charts. So instead, I'll just post what would've probably been my #1's during each month. Based off of what I would've been into at the time. And also based on what brings back the most memories of my childhood.... especially once I go before 2002.
2004 (11/12 years old)
December: Gwen Stefani - What You Waiting For
November: Kelly Clarkson - Breakaway
October: Destiny's Child - Lose My Breath
September: Black Eyed Peas - Let's Get It Started
August: Avril Lavigne - My Happy Ending
July: Nina Sky - Move Ya Body
June: Beyonce - Naughty Girl
May: Usher - Burn
April: Usher - Yeah
March: Britney Spears - Toxic
February: Linkin Park - Numb
January: Outkast - Hey Ya!
2003 (10/11 years old)
December: Black Eyed Peas - Shut Up
November: Nelly Furtado - Powerless (Say What You Want)
October: Beyonce / Sean Paul - Baby Boy
September: Black Eyed Peas - Where Is The Love?
August: Keisha Chante - Unpredictable
July: Beyonce - Crazy In Love
June: Evanescence - Bring Me To Life
May: Sean Paul - Get Busy
April: t.A.T.u - All The Things She Said
March: Justin Timberlake - Cry Me A River
February: P!nk - Family Portrait
January: Jennifer Lopez - Jenny From The Block
2002 (9/10 years old)
December: Avril Lavigne - I'm With You
November: Eminem - Lose Yourself
October: Coldplay - In My Place
September: Nelly / Kelly Rowland - Dilemma
August: P!nk - Just Like A Pill
July: Jimmy Eat World - The Middle
June: Vanessa Carlton - A Thousand Miles
May: Avril Lavigne - Complicated
April: P!nk - Don't Let Me Get Me
March: Linkin Park - In The End
February: Kylie Minogue - Can't Get You Out Of My Head
January: P!nk - Get The Party Started
2001 (8/9 years old)
December: Enrique Iglesias - Hero
November: Mary J Blige - Family Affair
October: Staind - It's Been A While
September: Blu Cantrell - Hit Em Up Style
August: Destiny's Child - Bootylicious
July: Train - Drops Of Jupiter
June: Christina Aguilera - Lady Marmalade
May: Nelly - Ride Wit Me
April: Crazy Town - Butterfly
March: Lenny Kravitz - Again
February: Jennifer Lopez - Love Don't Cost A Thing
January: Shaggy - It Wasn't Me
2000 (7/8 years old)
December: Destiny's Child - Independent Women
November: Mya - Case Of The Ex
October: 3 Doors Down - Kryptonite
September: Madonna - Music
August: Matchbox 20 - Bent
July: *NSYNC - It's Gonna Be Me
June: Britney Spears - Oops I Did It Again
May: Destiny's Child - Say My Name
April: Macy Gray - I Try
March: Santana - Maria Maria
February: *NSYNC - Bye Bye Bye
January: Eiffel 65 - Blue (Da Ba Dee)
1999 (6/7 years old)
December: Jennifer Lopez - Waiting For Tonight
November: Santana - Smooth
October: Mariah Carey - Heartbreaker
September: Christina Aguilera - Genie In A Bottle
August: Len - Steal My Sunshine
July: Tal Bachman - She's So High
June: Backstreet Boys - I Want It That Way
May: Shania Twain - That Don't Impress Me Much
April: Sixpence None The Richer - Kiss Me
March: Cher - Believe
February: Britney Spears - Baby One More Time
January: Lenny Kravitz - Fly Away
1998 (5/6 years old)
December: Alanis Morissette - Thank U
November: Goo Goo Dolls - Slide
October: Sheryl Crow - My Favourite Mistake
September: Jennifer Paige - Crush
August: Goo Goo Dolls - Iris
July: Madonna - Ray Of Light
June: Shania Twain - You're Still The One
May: Fastball - The Way
April: Natalie Imbruglia - Torn
March: Savage Garden - Truly Madly Deeply
February: The Verve - Bittersweet Symphony
January: Backstreet Boys - As Long As You Love Me
1997 (4/5 years old)
December: Chumbawumba - Tubthumping
November: Spice Girls - Spice Up Your Life
October: Robyn - Show Me Love
September: Aqua - Barbie Girl
August: Backstreet Boys - Quit Playing Games
July: Third Eye Blind - Semi Charmed Life
June: Hanson - MMMBop
May: Spice Girls - Say You'll Be There
April: Cardigans - Love Fool
March: Wallflowers - One Headligh
tFebruary: Spice Girls - Wannabe
January: No Doubt - Don't Speak
... and that's about as far back as my memory will likely go. But I think my radio station must've played a lot of older songs because I do remember some 1996 stuff... Hmm. But I want to complete my lifetime.
1996 (3/4 years old)
December: Alanis Morissette - Head Over Feet
November: Sheryl Crow - If It Makes You Happy
October: Celine Dion - It's All Coming Back
September: Donna Lewis - I Love You Always Forever
August: Alanis Morissette - You Learn
July: The Fugees - Killing Me Softly
June: Mariah Carey - Always Be My Baby
May: Celine DIon - Because You Loved Me
April: Alanis Morrissette - Ironic
March: Everything But The Girl - Missing
February: Ace Of Base - Beautiful Life
January: Alanis Morissette - Hand In My Pocket
^ I definitely remember hearing all of those
1995 (2/3 years old)
December: Deep Blue Something - Breakfast At Tiffany's (even though I hate this song)
November: Take That - Back For Good
October: Mariah Carey - Fantasy
September: Seal - Kiss From A Rose
August: TLC - Waterfalls
July: Blues Traveler - Run Around
June: Montell Jordan - This Is How We Do It
May: Real McCoy - Run Away
April: Dionne Farris - I Know
March: Green Day - When I Come Around
February: Des'ree - You Gotta Be
January: Bon Jovi - Always
^ just the ones that bring back the most memories
1994 (1/2 years old)
December: Real McCoy - Another Night
November: Melissa Etheridge - I'm The Only One
October: Sheryl Crow - All I Wanna Do
September: Collective Soul - Shine
August: Lisa Loeb - Stay
July: Ace Of Base - Don't Turn Around
June: All-4-One - I Swear
May: Counting Crows - Mr Jones
April: Ace Of Base - The Sign
March: Celine Dion - The Power Of Love
February: Bryan Adams etc - All For Love
January: Bryan Adams - Please Forgive Me
^ same
'1'993
December: Ace Of BAse - All That She Wants
November: Meat Loaf - I'd Do Anything For Love
October: Billy Joel - River Of Dreams
September: Soul Asylum - Runaway Train
August: Proclaimers - I'm Gonna Be
July: UB40 - Can't Help Falling In Love
June: Inner Circle - Bad Boys
May: Spin Doctors - Two Princes
April: Bon Jovi - Bed Of Roses
March: Peabo Bryson - A Whole New World
February: Whitney Houston - I'm Every Woman
January: Snap! - Rhythm Is A Dancer
^ and now I'm really stretching it for memories
1992
December: Whitney Houston - I Will Always Love You
November: Heights - How Do You Talk To An Angel
October: Patty Smith - Sometimes Love Just Ain't Enough
September: Shakespeare's Sister - Stay
August: Guns N Roses - November Rain
July: Tom Cochrane - Life Is A Highway
June: Kris Kross - Jump
^ and here too. But that completes that.