Donald Trump's 1999 Pick-Up Lines, Revealed!

S3 2:08
Brooke Shields revealed the details of her conversation with Donald Trump which he asked her out immediately after his 1999 divorce. Stephen reveals the pick-up lines he used on the other '90s female celebrities. Air Date: Oct 6, 2017
Weeknights at 11:35/10:35c

Full Episodes

The Late Show with Stephen Colbert - 12/14/18 (Tony Shalhoub, Joe Wong)
S4 E66 Dec 14, 2018
12/14/18 (Tony Shalhoub, Joe Wong)
The Late Show with Stephen Colbert - 12/13/18 (Diane Kruger, Rep. Joaquin Castro, Secretary Julian Castro, Ira Madison III)
S4 E65 Dec 13, 2018
12/13/18 (Diane Kruger, Rep. Joaquin Castro, Secretary Julian Castro, Ira Madison III)
The Late Show with Stephen Colbert - 12/12/18 (Leslie Mann, Brandon Micheal Hall, Lil Wayne)
S4 E64 Dec 12, 2018
12/12/18 (Leslie Mann, Brandon Micheal Hall, Lil Wayne)
The Late Show with Stephen Colbert - 12/11/18 (Whoopi Goldberg, Adam Pally, Jungle)
S4 E63 Dec 11, 2018
12/11/18 (Whoopi Goldberg, Adam Pally, Jungle)
The Late Show with Stephen Colbert - 12/10/18 (Bryan Cranston, Doris Kearns Goodwin)
S4 E62 Dec 10, 2018
12/10/18 (Bryan Cranston, Doris Kearns Goodwin)
The Late Show with Stephen Colbert - 12/7/18 (Kathy Griffin, Emma Willmann)
S4 E61 Dec 07, 2018
12/7/18 (Kathy Griffin, Emma Willmann)
The Late Show with Stephen Colbert - 12/6/18 (Senator Bernie Sanders, Chris Gethard)
S4 E60 Dec 06, 2018
12/6/18 (Senator Bernie Sanders, Chris Gethard)
S4 E59 Dec 05, 2018
12/5/18 (Jeff Daniels, Emily Mortimer)
S4 E58 Dec 04, 2018
12/4/18 (Julia Roberts, Patrick Wilson)
S4 E57 Dec 03, 2018
12/3/18 (Catherine Zeta-Jones, Lucas Hedges, Nathaniel Rateliff & the Night Sweats)
S4 E56 Nov 30, 2018
11/30/18 (Michelle Obama, Common)
S4 E55 Nov 29, 2018
11/29/18 (Garth Brooks, Tim Meadows)
Show More