Late Show with David Letterman · SEASON 16
Will Smith, Of Montreal
Episode 62 · 2008-12-18

- Talk
- Comedy
Episode overview
Will Smith and Of Montreal are the scheduled guests.
Season 16 episodes
1. Nicolas Cage, Anna Torv, Terrence Howard2008-09-02
2. Dr. Phil McGraw, Tilda Swinton, Tricky2008-09-03
3. Robin Williams, Shannen Doherty, Duffy2008-09-04
4. John Malkovich, Hayden Panettiere, Steve Earle2008-09-05
5. Keira Knightley, Thomas L. Friedman2008-09-08
6. Jada Pinkett Smith, Chris Russo, Michael Buble2008-09-09
7. Sen. Barack Obama, LeBron James2008-09-10
8. Jessica Simpson, Jack Hanna2008-09-11
9. Meg Ryan, Ricky Gervais2008-09-12
10. Bill Clinton, Chris Rock2008-09-22
11. Julianne Moore, Tom Dreesen & Tim Reid, Kings of Leon2008-09-23
12. Keith Olbermann, Chandra Wilson, Delta Goodrem2008-09-24
13. Paris Hilton, Usain Bolt, Morningwood2008-09-25
14. Lance Armstrong, Kristen Wiig, TV on the Radio2008-09-26
15. Julia Louis-Dreyfus, Michael Cera, Pete Seeger2008-09-29
16. Anne Hathaway, Josette Sheeran, The Virgins2008-09-30
17. Kate Walsh, Barry Sonnenfeld, Darius Rucker2008-10-01
18. Calista Flockhart, Bill Hader, Lucinda Williams2008-10-02
19. Brian Williams, Tim Robbins2008-10-03
20. Russell Crowe, Sarah Vowell, The Pretenders2008-10-06
21. Debra Messing, John Carter, Tegan & Sara2008-10-07
22. Dennis Quaid, Sarah Chalke, Buddy Guy2008-10-08
23. Bill Murray, Beck2008-10-09
24. Jeremy Piven, Elizabeth Banks, Lou Reed2008-10-10
25. Sarah Silverman, the Teutuls, Ra Ra Riot2008-10-13
26. Josh Brolin, Amy Sedaris, Blues Traveler2008-10-14
27. Martin Short, Marv Albert2008-10-15
28. Sen. John McCain, Ne-Yo2008-10-16
29. Tina Fey, Frank Caliendo, Tim Montana2008-10-17
30. Bill O'Reilly, Lauren Conrad2008-10-27
31. Regis Philbin, James Taylor2008-10-28
32. Alec Baldwin, Paul Mooney, Ryan Adams2008-10-29
33. Ashley Olsen, Paul Rudd, John Legend2008-10-30
34. Marcia Cross, Alan Zweibel2008-10-31
35. Paris Hilton, Elvis Costello, Jenny Lewis, a Top Ten List by Ricky Gervais2008-11-03
36. Tom Brokaw, Vera Farmiga2008-11-05
37. Ben Stiller, Q-Tip2008-11-06
38. Natalie Portman, Artie Lange, Brad Paisley2008-11-07
39. Ted Turner, Jamie Oliver, Taylor Swift2008-11-10
40. Don Rickles, Amy Brenneman, Alicia Keys2008-11-11
41. Russell Brand, Charlie Haden2008-11-12
42. Bruce Willis, Sia2008-11-13
43. Bill Cosby, Matt Braunger2008-11-14
44. Emma Thompson, Michelle Felicetta, Purple Reign2008-11-17
45. Carla Bruni Sarkozy, Jack Hanna, Cold Hard Cash2008-11-18
46. Katie Couric, Dev Patel, Mr. Brownstone2008-11-19
47. Stephen Colbert, Kristen Stewart, Super Diamond2008-11-20
48. James Franco, Bruce McCall, The Allstarz2008-11-21
49. Nicole Kidman, Simon Baker, Kanye West2008-11-24
50. Reese Witherspoon, Harry Connick Jr.2008-11-25
51. Teri Hatcher, Ludacris2008-11-26
52. Denis Leary, John Mayer2008-11-27
53. Tom Arnold, Faith Hill2008-11-28
54. Jennifer Connelly, Anderson Cooper, The Duke Spirit2008-12-08
55. Amy Adams, Michael Sheen, Jamey Johnson2008-12-09
56. Keanu Reeves, Paula Abdul, Loudon Wainwright III2008-12-10
57. Sen. John McCain, Bon Iver2008-12-11
58. Meryl Streep, Jeff Altman2008-12-12
59. Adam Sandler2008-12-15
60. Tom Cruise, Fall Out Boy2008-12-16
61. Jennifer Aniston, Broken Social Scene2008-12-17
62. Will Smith, Of Montreal2008-12-18
63. Jerry Seinfeld, Leona Lewis2008-12-19
64. Dustin Hoffman, Todd Rundgren2008-12-22
65. Jay Thomas, Mickey Rourke, Darlene Love2008-12-23
66. Tracy Morgan, Matt Braunger2008-12-26
67. Kate Hudson, Glasvegas2009-01-05
68. Kevin James, Becky Quick, Erin McCarley2009-01-06
69. Ricky Gervais, Rose Byrne, Okkervil River2009-01-07
70. Kate Winslet, Marv Albert2009-01-08
71. Kiefer Sutherland, Wendy Liebman2009-01-09
72. Billy Crystal, Kara DioGuardi2009-01-12
73. Salma Hayek, Jimmie Walker2009-01-13
74. Clint Eastwood, Randy Rogers Band2009-01-14
75. Kyra Sedgwick, Gwen Ifill2009-01-15
76. Zach Braff, Arj Barker, The Airborne Toxic Event2009-01-16
77. Brian Williams, Ben Kweller2009-01-26
78. Evangeline Lilly, Seth Meyers, Andrew Bird2009-01-27
79. Lauren Graham, Guy Fieri, MENEW2009-01-28
80. Renee Zellweger, Tony Dungy, Graham Nash sits in with the band2009-01-29
81. Mary Hicks, the Gaslight Anthem2009-01-30
82. Ben Roethlisberger, Steve Martin2009-02-02
83. Rod Blagojevich, Richard Jenkins2009-02-03
84. Joe Torre, Demetri Martin, Lyle Lovett and John Hiatt2009-02-04
85. Isla Fisher, extreme fisherman Matt Watson, Mark Olson and Gary Louris, a Top Ten List presented by Lil' Wayne2009-02-05
86. Dakota Fanning, Keith Alberstadt, Beirut2009-02-06
87. Naomi Watts, Danny McBride, 2009 Sports Illustrated Swimsuit Issue cover reveal2009-02-09
88. The crew of US Airways "Miracle On The Hudson" Flight 1549, Heartless Bastards2009-02-10
89. Joaquin Phoenix, Bar Refaeli, Anthony Hamilton2009-02-11
90. Chris Russo, the Jonas Brothers, Ashford & Simpson2009-02-12
91. Martha Stewart, Jake Johannsen, Matt Nathanson2009-02-13
92. Ellen Pompeo, Daytona 500 winner Matt Kenseth, Willie Nelson with Asleep at the Wheel2009-02-16
93. Bonnie Hunt, M. Ward2009-02-17
94. Donald Trump, Antony and the Johnsons2009-02-18
95. David Spade, Jeffrey Sachs, David Sanborn with Sam Moore2009-02-19
96. Barbara Walters, Mike Birbiglia, Shemekia Copeland2009-02-20
97. Katie Couric, U22009-03-02
98. Felicity Huffman, Artie Lange, U22009-03-03
99. Dr. Phil McGraw, U22009-03-04
100. Jon Stewart, U2, a Top Ten List featuring 10 Team USA members from the World Baseball Classic2009-03-05
101. Jason Segel, Brian Kiley, U22009-03-06
102. Russell Brand, Jack Hanna2009-03-09
103. Stupid Pet Tricks, Paul Rudd, Razorlight2009-03-10
104. Tom Brokaw, An Horse2009-03-11
105. Andy Samberg, Paul Teutul Sr., the Broadway cast of "West Side Story"2009-03-12
106. Will Ferrell, Cursive2009-03-13
107. Nicolas Cage, Rachel Maddow2009-03-16
108. Julia Roberts, Bell X12009-03-17
109. Craig Ferguson, Ginnifer Goodwin, Modest Mouse2009-03-18
110. Billy Crystal, Kara DioGuardi, a Top Ten List presented by Owen Wilson2009-03-19
111. David Spade, Richard Zoglin, David Sanborn and Sam Moore2009-03-20
112. Hugh Laurie, Bloc Party2009-03-23
113. Mary Tyler Moore, Blake Lively, White Lies2009-03-24
114. Christina Applegate, Jim Gaffigan, Jesse Harris with Norah Jones2009-03-25
115. Seth Rogen, Tom Dreesen, Adele2009-03-30
116. Bill O'Reilly, Marianne Faithfull2009-03-31
117. Marg Helgenberger, Francisco Palacios, Ray LaMontagne2009-04-01
118. Michael J. Fox, the Fray2009-04-02
119. Denis Leary, Diana Krall2009-04-03
120. Zac Efron, Mike Golic and Mike Greenberg, A.C. Newman with Nicole Atkins2009-04-13
121. Kelly Ripa, Bill Scheft, Yeah Yeah Yeahs2009-04-14
122. Drew Barrymore, Jack McBrayer, Neko Case2009-04-15
123. Matthew Perry, Elisha Cuthbert, Rascal Flatts2009-04-16
124. Russell Crowe, Joe Wong2009-04-17
125. Jeff Goldblum, Jeff Dunham2009-04-20
126. Nathan Lane, Tinted Windows2009-04-21
127. Beyonce, Jim Parsons2009-04-22
128. Jamie Foxx, Lauren Conrad, the Dead2009-04-23
129. Michael Keaton, Lily Allen2009-04-24
130. Matthew Fox, Carol Leifer, the All-American Rejects, a Top Ten List presented by Matthew Stafford2009-04-27
131. Dolly Parton, Zachary Quinto2009-04-28
132. Jennifer Garner, Tesla Motors CEO Elon Musk, Manchester Orchestra2009-04-29
133. Regis Philbin, a performance by the Broadway cast of "Hair"2009-04-30
134. Kiefer Sutherland, Jim Norton, Bat for Lashes2009-05-01
135. Gordon Ramsay, Chris Pine, Keri Hilson with Kanye West2009-05-04
136. Liev Schreiber, Dr. Sanjay Gupta, Franz Ferdinand2009-05-05
137. Bruce Willis, Ben Harper & Relentless72009-05-06
138. Norm MacDonald, a Top Ten List presented by Leonard Nimoy, Animal Collective2009-05-07
139. Matthew Broderick, Brian Regan, Chris Cornell2009-05-08
140. Tom Hanks, the Killers2009-05-11
141. Alec Baldwin, Maya Rudolph, Chrisette Michele2009-05-12
142. Robin Williams, Wynton Marsalis2009-05-13
143. Kid Scientists, Teri Hatcher, Rick Ross with Magazeen, a Top Ten List presented by Ron Howard2009-05-14
144. John Goodman, Tommy Tiernan, Mastodon2009-05-15
145. Ben Stiller, White Rabbits2009-05-18
146. Jane Fonda, Piedmont Bird Callers, Kenny Chesney2009-05-19
147. Stephen Colbert, General Motors Vice Chairman Bob Lutz, Grizzly Bear2009-05-20
148. Amy Sedaris, Ed Helms, Jean Redpath2009-05-21
149. Ricky Gervais, Green Day2009-05-22
150. Bill Cosby, Helio Castroneves, Melody Gardot2009-06-01
151. Jack Hanna, John Krasinski2009-06-02
152. Jessica Biel, Zach Galifianakis, Steve Earle2009-06-03
153. Elvis Costello, a Top Ten List presented by Neil Patrick Harris2009-06-04
154. Paris Hilton, Calvin Borel, Steven Wright2009-06-05
155. Howard Stern, Mos Def2009-06-08
156. Julia Roberts, Black Eyed Peas2009-06-09
157. Kathy Griffin, Stupid Human Tricks, Sonic Youth, an NBA Finals report by Phoenix Suns' Steve Nash2009-06-10
158. Denzel Washington, the Jonas Brothers, a Top Ten List with Regis Philbin2009-06-11
159. Sandra Bullock, Pete Correale, P.J. Harvey & John Parish2009-06-12
160. Jack Black, M.A. Sanjayan2009-06-15
161. Michelle Pfeiffer, Judah Friedlander, Ian McLagan & the Bump Band2009-06-16
162. Ryan Reynolds, Padma Lakshmi, the Eels2009-06-17
163. Danny DeVito, Bear Grylls, Phoenix2009-06-18
164. Jada Pinkett Smith, Michael Cera, the Sounds2009-06-19
165. Samuel L. Jackson, Emeril Lagasse, Iggy Pop & the Brighton Port Authority2009-06-22
166. Sandra Day O'Connor, MSTRKRFT with John Legend, a Top Ten List presented by Lucas Glover2009-06-23
167. Ray Romano, St. Vincent2009-06-24
168. Johnny Depp, Megan Fox2009-06-25
169. Martin Short, Regina Spektor2009-06-26
170. Serena Williams, Hayden Panettiere, Conor Oberst and the Mystic Valley Band2009-07-06
171. Sacha Baron Cohen, Joel McHale2009-07-07
172. Queen Latifah, Emma Watson2009-07-08
173. Daniel Radcliffe, Veronika Part, Levon Helm, a Top Ten List presented by Bruno2009-07-09
174. Rainn Wilson, Larry Miller, Maxwell2009-07-10
175. Jonah Hill, Gar Ryness, Kelly Clarkson2009-07-13
176. Edie Falco, Michael Showalter, Wilco with Feist2009-07-14
177. Paul McCartney, a Top Ten List presented by Bruce Willis2009-07-15
178. Anderson Cooper, Anna Paquin, Grizzly Bear2009-07-16
179. Tom Arnold, Metric, a Top Ten List presented by Dave's mom Dorothy2009-07-17
180. Katherine Heigl, Jeff Altman, Spinnerette2009-07-20
181. Kevin Spacey, Jesse James, the Flatlanders, a Top Ten List presented by Stewart Cink2009-07-21
182. Tracy Morgan, Leslie Mann, Diane Birch2009-07-22
183. Sean "Diddy" Combs, Vera Farmiga, Ginuwine with Missy Elliott2009-07-23
184. Amy Poehler, Nick Griffin, Judy Collins2009-07-24
185. Eric Bana, Dave Matthews Band, a Top Ten List presented by Chicago White Sox star Mark Buehrle2009-07-27
186. Katie Couric, Silversun Pickups2009-07-28
187. Amy Adams, Tom Dreesen, Elbow2009-07-29
188. Adam Sandler, Cage the Elephant2009-07-30
189. Regis Philbin, Ted Alexandro, Dave Matthews Band2009-07-31
190. Quentin Tarantino, Eric Ripert, Robert Cray2009-08-17
191. Donald Trump, Diane Kruger, Billy Currington, a Top Ten List presented by Britney Spears2009-08-18
192. Mike Myers, Ken Burns2009-08-19
193. Anna Wintour, Mark Teixeira2009-08-24
194. Renee Zellweger, Gary Mule Deer2009-08-20
195. Christina Applegate, Brendan Benson, Patton Oswalt2009-08-21
196. Anna Wintour, Mark Teixeira2009-08-24
197. Mary-Louise Parker, Eugene Levy, Jet2009-08-25
198. Anne Heche, Jim Parsons, Care Bears on Fire2009-08-26
199. Andy Roddick, Rachael Ray, Mutemath2009-08-27
200. Artie Lange, Todd Barry, Imogen Heap2009-08-28