I'm going to try to answer these only with Beatle songs
A song that needs to be played very loud "Back in the USSR"
A song that makes you want to dance "Twist and Shout"
A song to drive to "Drive My Car"
A song with a number in the title "One After 909"
A song that makes you happy "All My Loving"
A song that makes you sad "Let It Be"
A song that reminds you of summer "Penny Lane"
A song that you remember from your childhood "She Loves You"
A song that breaks your heart "Two of Us"
A song that you never get tired of "Good Day, Sunshine"
A song from your preteen year "Yellow Submarine"
A song that is a cover by another artist "Long Tall Sally"
A song from the year you were born Stymied by this one. "Jailhouse Rock" (After all, the Lads loved The King.)
A song that makes you think about life "The Long and Winding Road"
Your favourite song with a persons name in the title "Rocky Raccoon"
A song that you think everyone should listen to "Eleanor Rigby"
A song by a band you wish were still together "Can't Buy Me Love"
A song by an artist no longer living "Help!"
A song by an artist with a voice you love "You're Gonna Lose that Girl" (I love the harmonies on this. "Watch what you do, yeah ...")