5 titles.

1. Zoolander 2 (2016)
And finally tonight, here's something to make you feel old. Incredible as it may sound, of the over 3.7 million high school graduates this year, less than 2% can tell you what a fax machine is, name a Caucasian president, or know who Derek Zoolander was!
Who says swimsuit models are useless? Take me from behind, Zoolander. Grab on for safety... and buoyancy! We're going to swim to Rome.
2. Ted 2 (2015)
Skywalker, Solo, Vader, Kenobi, Palpatine, Calrissian, Balboa, Rambo, Griswold, Stepford, Bickle, Gump, Corleone, Wonka, Lebowski, Venkman, Spengler, Stantz, Rizzo, Zuko, Golighty, Higgins, Dolittle, Poppins, Bond, Blofeld, Blutarsky, Soze, O'Hara, Butler, McFly, Plissken, Ventura, Burgundy, Scissorhands, Drebin, Bueller, Lecter, Dumbledore, Sparrow, Doubtfire, Bourne, Von Trapp, Zoolander, Kirk, Spock, McCoy...
3. Zoolander (2001)
So join now, 'cause at the Derek Zoolander Center For Kids Who Can't Read Good And Wanna Learn To Do Other Stuff Good Too, we teach you that there's more to life than just being really, really, really good looking. Right kids?
SHUT UP! Enough already, Ballstein! Who cares about Derek Zoolander anyway? The man has only one look, for Christ's sake! Blue Steel? Ferrari? Le Tigra? They're the same face! Doesn't anybody notice this? I feel like I'm taking crazy pills! I invented the piano key necktie, I invented it! What have you done, Derek? You've done nothing! NOTHIIIING! And I will be a monkey's uncle if I let you ruin this for me, because if you can't get the job done, then I will!
I suggest you and your Kmart Jaclyn Smith Collection outfit... stay the hell away from Derek Zoolander!
...for the past four years, male modeling has had a shadow cast over it by one man and five syllables: Der-ek Zoo-land-er.
4. Derek Zoolander University (1997 Short Film)
Hi. I'm Derek Zoolander, president and model and founder and dean and CEO of the Derek Zoolander University of Modeling for Men.
5. Circle the Wagen (2013 Documentary)
Taking a shower in gasoline is not fun, despite what Zoolander would have you believe.
5 titles.