He is the oldest son of Grammy winning artist Kenny Loggins and his first wife, Eva Ein.
He was constantly surrounded by his father's celebrity friends such as Jackson Browne, Graham Nash, Michael McDonald and Glen Phillips of Toad the Wet Sprocket.
Crosby was offered to appear on the MTV reality show Rock the Cradle in the beginning of 2008, which tried to determine which musically successful parents had the most talented children.
Kenny chose "I Don't Wanna Be" by Gavin Degraw for Crosby to sing.
Crosby was nervous that since this song was not his usual genre, the "audience would pick up on that", despite his father's utmost confidence in him.
(individually 7.5, 7.5, 10, 9) He received a perfect 10 from judge June Ambrose for his sex appeal and a low score of 7.5 from judge Belinda Carlisle because she claimed he was awkward and called his performance "frat-rock" He, once again, did not receive a place in the untouchable chair and was up for elimination.
He broke out the electric guitar and drove the crowd crazy with his rendition of "Long Road To Ruin" by the Foo Fighters.
After a near perfect score, Crosby was given a seat in the untouchable chair and will automatically be performing Week 5, which is also the last night to vote and the three remaining contestants will be in the finale.
He lost his ranking of highest scorer of the season to Jesse Blaze Snider, who received an almost perfect 39.
On the finale, Crosby redid "I'm Alright" with his father, Kenny Loggins, with him, and sang The Bravery's "Believe".
The show closed with confetti falling from the ceiling and Crosby receiving congrats from former contestants and friends.