21 actors have played Herbie in Gypsy.
| Performer | Production | Opened |
|---|---|---|
| Jack Klugman | Broadway Gypsy | 1959 |
| Alfred Sandor | US Tour Gypsy | 1961 |
| Joseph Leon | US Tour Gypsy | 1961 |
| Barrie Ingham | West End Gypsy | 1973 |
| Ed Riley | Broadway Gypsy | 1974 |
| Rex Robbins | Broadway Gypsy | 1974 |
| John Hallow | Milburn, NJ (Regional) Gypsy | 1976 |
| Jamie Ross | Broadway Gypsy | 1989 |
| Jonathan Hadary | Broadway Gypsy | 1989 |
| Mace Barrett | Broadway Gypsy | 1989 |
| Lenny Wolpe | Milburn, NJ (Regional) Gypsy | 1998 |
| John Dossett | Broadway Gypsy | 2003 |
| Michael McCormick | Broadway Gypsy | 2003 |
| William Parry | Broadway Gypsy | 2003 |
| Jack Willis | Gypsy | 2006 |
| John Sloman | St. Louis, MO (Regional) Gypsy | 2006 |
| Boyd Gaines | Off-Broadway Gypsy | 2007 |
| Boyd Gaines | Broadway Gypsy | 2008 |
| Jim Bracchitta | Broadway Gypsy | 2008 |
| Scott Ripley | Regional (US) Gypsy | 2014 |
| Peter Davidson | West End Gypsy | 2015 |
| Danny Burstein | Broadway Gypsy | 2024 |
Other Roles in Gypsy
| Role | Production | Opened |
|---|---|---|
| Agnes | St. Louis, MO (Regional) Gypsy | 2006 |
| Angie | St. Louis, MO (Regional) Gypsy | 2006 |
| Baby June | St. Louis, MO (Regional) Gypsy | 2006 |
| Baby Louise | St. Louis, MO (Regional) Gypsy | 2006 |
| Cigar | St. Louis, MO (Regional) Gypsy | 2006 |
| Dallas | St. Louis, MO (Regional) Gypsy | 2006 |
| Electra/Miss Cratchitt | St. Louis, MO (Regional) Gypsy | 2006 |
| George/Pastey | St. Louis, MO (Regional) Gypsy | 2006 |
| Herbie | St. Louis, MO (Regional) Gypsy | 2006 |
| Hollywood Blonde | St. Louis, MO (Regional) Gypsy | 2006 |
| June | St. Louis, MO (Regional) Gypsy | 2006 |
| Kringelein/Phil | St. Louis, MO (Regional) Gypsy | 2006 |
| L.A. | St. Louis, MO (Regional) Gypsy | 2006 |
| Louise | St. Louis, MO (Regional) Gypsy | 2006 |
| Maid | St. Louis, MO (Regional) Gypsy | 2006 |
| Mazeppa | St. Louis, MO (Regional) Gypsy | 2006 |
| Newsboy | St. Louis, MO (Regional) Gypsy | 2006 |
| Pop | St. Louis, MO (Regional) Gypsy | 2006 |
| Rose | St. Louis, MO (Regional) Gypsy | 2006 |
| Tessie Tura | St. Louis, MO (Regional) Gypsy | 2006 |
| Tulsa | St. Louis, MO (Regional) Gypsy | 2006 |
| Uncle Jocko/Bourgeron-Cochon | St. Louis, MO (Regional) Gypsy | 2006 |
| Weber/Mr. Goldstone | St. Louis, MO (Regional) Gypsy | 2006 |
| Yonkers | St. Louis, MO (Regional) Gypsy | 2006 |
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