What 38 Celebs Looked Like In Their Teenage Dirtbag Era

Jake Gyllenhaal when he was in his “teenage dirtbag” phase:

2.

Justin Timberlake now:

Justin Timberlake when he was in his “teenage dirtbag” phase:

Prince Harry when he was in his “teenage dirtbag” phase:

Tony Hawk when he was in his “teenage dirtbag” phase:

Ashton Kutcher when he was in his “teenage dirtbag” phase:

Aaron Paul when he was in his “teenage dirtbag” phase:

Zac Efron when he was in his “teenage dirtbag” phase:

Drake when he was in his “teenage dirtbag” phase:

Miley Cyrus when she was in her “teenage dirtbag” phase:

Ryan Gosling when he was in his “teenage dirtbag” phase:

11.

Leonardo DiCaprio now:

Leonardo DiCaprio when he was in his “teenage dirtbag” phase:

Freddie Prinze Jr. when he was in his “teenage dirtbag” phase:

Kristen Stewart when she was in her “teenage dirtbag” phase:

Taylor Momsen when she was in her “teenage dirtbag” phase:

Ryan Reynolds when he was in his “teenage dirtbag” phase:

Justin Bieber when he was in his “teenage dirtbag” phase:

Taylor Swift when she was in her “teenage dirtbag” phase:

Ariana Grande when she was in her “teenage dirtbag” phase:

Kylie Jenner when she was in her “teenage dirtbag” phase:

Justin Long when he was in his “teenage dirtbag” phase:

Chris Evans when he was in his “teenage dirtbag” phase:

Rider Strong when he was in his “teenage dirtbag” phase:

Devon Sawa when he was in his “teenage dirtbag” phase:

Paris Hilton when she was in her “teenage dirtbag” phase:

Nicole Richie when she was in her “teenage dirtbag” phase:

26.

Dylan and Cole Sprouse now:

Dylan and Cole Sprouse when they were in their “teenage dirtbag” phase:

Hilary Duff when she was in her “teenage dirtbag” phase:

Lindsay Lohan when she was in her “teenage dirtbag” phase:

Ashley Tisdale when she was in her “teenage dirtbag” phase:

Joe Jonas when he was in his “teenage dirtbag” phase:

Kelly Osbourne when she was in her “teenage dirtbag” phase:

Kelly Ripa when she was in her “teenage dirtbag” phase:

Avril Lavigne when she was in her “teenage dirtbag” phase:

Madonna when she was in her “teenage dirtbag” phase:

Ashlee Simpson when she was in her “teenage dirtbag” phase:

Lorde when she was in her “teenage dirtbag” phase:

Jared Leto when he was in his “teenage dirtbag” phase:

38.

And last but not least, Pete Davidson now:

Pete Davidson when he was in his “teenage dirtbag” phase: