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| Date | Grid | Clue | Author |
|---|---|---|---|
| Tuesday, May 7, 2013 | 16A | Vagrant (3) | Jeff Chen |
| Thursday, May 2, 2013 | 10D | Wandering soul (2) | Josh Knapp |
| Friday, February 3, 2012 | 5A | Drifting type | Joel Kaplow |
| Thursday, May 19, 2011 | 15A | One who's left holding the bag? | Paula Gamache |
| Saturday, September 25, 2010 | 46D | Depression-era traveler | Patrick Berry |
| Sunday, August 15, 2010 | 9D | Red Skelton persona (2) | Daniel C. Bryant |
| Monday, June 22, 2009 | 39A | Vagrant (3) | Fred Piscop |
| Tuesday, February 24, 2009 | 38A | Bum | Stephen Edward Anderson |
| Saturday, September 27, 2008 | 54D | Great Depression figure | Karen M. Tracey |
| Tuesday, May 20, 2008 | 14A | Boxcar hopper | Billie Truitt |
| Monday, May 12, 2008 | 33D | Tramp (7) | Randall J. Hartman |
| Tuesday, December 4, 2007 | 29D | Boxcar rider | Alison Donald |
| Saturday, February 24, 2007 | 38A | Derelict | Byron Walden |
| Wednesday, October 18, 2006 | 26D | Vagabond | John Farmer |
| Tuesday, February 21, 2006 | 15A | Tramp (7) | Lisa Wiseman |
| Friday, July 29, 2005 | 57D | Sundowner (2) | Kyle Mahowald |
| Tuesday, November 25, 2003 | 59D | King of the road (3) | Allan E. Parrish |
| Sunday, October 12, 2003 | 66D | Wanderer (5) | David J. Kahn |
| Sunday, September 28, 2003 | 57A | Old-fashioned camp resident | Brendan Emmett Quigley |
| Tuesday, September 9, 2003 | 53D | Nonpaying train passenger | Robert Zimmerman |
| Thursday, February 20, 2003 | 7D | Wanderer (5) | Peter Sarrett |
| Wednesday, December 26, 2001 | 9D | One who rides the rails | Ed Early |
| Sunday, December 16, 2001 | 109D | Wanderer (5) | Fred Piscop |
| Wednesday, July 11, 2001 | 53D | Odd jobs doer | Richard Silvestri |
| Thursday, May 3, 2001 | 59D | Transient | Trip Payne |
| Saturday, April 28, 2001 | 25A | Wanderer (5) | Rich Norris |
| Wednesday, March 28, 2001 | 6A | Bindle bearer (2) | Elizabeth C. Gorski |
| Monday, June 26, 2000 | 2D | Penniless person | Peter Gordon |
| Wednesday, April 26, 2000 | 15A | Wandering sort | A. J. Santora |
| Thursday, April 20, 2000 | 52D | Rail rider | Nelson Hardy |
| Thursday, October 28, 1999 | 30D | Penniless traveler | Patrick D. Berry |
| Tuesday, August 31, 1999 | 14A | King of the road (3) | Arthur S. Verdesca |
| Friday, April 9, 1999 | 51A | One for the road | Manny Nosowsky |
| Friday, January 15, 1999 | 31D | Bindle bearer (2) | John Wolting |
| Tuesday, December 29, 1998 | 22D | Tramp (7) | Susan Harrington Smith |
| Friday, September 25, 1998 | 24D | "Rolling stone" | Mark Blakeburn |
| Monday, September 7, 1998 | 58D | Tramp (7) | Gregory E. Paul |
| Wednesday, June 17, 1998 | 16A | Freight car hopper | Elizabeth C. Gorski |
| Tuesday, April 7, 1998 | 50D | Tracks traveler | Randy Sowell |
| Wednesday, November 26, 1997 | 14A | Tramp (7) | Nancy Schuster |
| Sunday, November 16, 1997 | 34A | Boxcar rider, maybe | Frank Longo |
| Wednesday, September 24, 1997 | 31D | Wandering soul (2) | Wayne Robert Williams |
| Monday, August 4, 1997 | 10A | Tramp (7) | Gregory E. Paul |
| Monday, July 28, 1997 | 7D | Traveling tramp | Patrick Jordan |
| Friday, April 11, 1997 | 21A | One asking for a handout | Manny Nosowsky |
| Thursday, January 16, 1997 | 15A | Ding-donger | W. R. Williams |
| Friday, January 10, 1997 | 53D | Wanderer (5) | A. J. Santora |
| Friday, November 29, 1996 | 17A | Red Skelton persona (2) | B. White |
| Thursday, November 7, 1996 | 50D | King of the road (3) | G. R. Ferguson |
| Monday, October 14, 1996 | 15A | Tramp (7) | R. White |
| Wednesday, February 28, 1996 | 57D | Bindlestiff | F.A. Longo |
| Friday, May 19, 1995 | 32D | Skelton character | Michael S. Maurer |
| Wednesday, March 22, 1995 | 7D | Vagrant (3) | David J. Kahn |
| Friday, April 8, 1994 | 2D | Sundowner (2) | David A. Rosen |
16 results for HOBO from older pre-Shortz puzzles.
| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Tuesday, June 9, 1992 | 16A | Drifter | Edwards | Maleska |
| Tuesday, December 3, 1991 | 32D | Bindlestiff | Pomerance | Maleska |
| Wednesday, September 18, 1991 | 15A | Rail rider | Kenneth Haxton | Maleska |
| Monday, August 5, 1991 | 36D | Rider of the rails | Bernice Gordon | Maleska |
| Wednesday, June 13, 1990 | 2D | Weary Willie | Patricia A. Cevaal | Maleska |
| Wednesday, November 22, 1989 | 42D | Roads scholar | Gayle Dean | Maleska |
| Tuesday, July 4, 1989 | 55D | Traveler sans tickets | Dale O. Burgener | Maleska |
| Thursday, September 1, 1988 | 15A | Bindlestiff | Judson G. Trent | Maleska |
| Monday, June 20, 1988 | 16A | Tramp | Sidney L. Robbins | Maleska |
| Friday, September 18, 1987 | 1D | Tramp | June A. Boggs | Maleska |
| Tuesday, September 8, 1987 | 49D | King of the road | Kenneth Witte | Maleska |
| Sunday, July 12, 1987 | 94D | Roads scholar | Louis Sabin | Maleska |
| Tuesday, May 26, 1987 | 6D | Railroad freeloader | Bernice Gordon | Maleska |
| Wednesday, December 18, 1985 | 48D | Man of the road | Mary C. Whitten | Maleska |
| Friday, September 6, 1985 | 7D | Bindlestiff | Peter Swift | Maleska |
| Thursday, April 18, 1985 | 59D | Bindlestiff | Eli Wesoff | Maleska |