Hello all! I am having some trouble, and at an impass, I reinstalled Oblivion twice from GOG yet everytime I start it, it will go the launcher menu and when I click play the game will not start. Any way to resolve this issue?

That you get to the launcher menu first is normal. What do you mean by "the game will not start"? Nothing happens? A crash to the desktop? An endless loop? An error message? ... Please describe exactly what you do and what you observe.
Moreover, it would be useful to get more information from you like your operating system and whether or not you try to launch Oblivion via Galaxy. You say you "re-installed Oblivion" (on the same PC, I suppose)? Did you un-install Oblivion before re-installing it? Are there old save games? Have you installed mods / unofficial patches after you had re-installed Oblivion? Have you restored old savegames? If yes, were they based on the same Oblivion configuration as your new one?
And, perhaps most importantly: Have you un-installed Oblivion completely before re-installing it? This includes removing the game folder, the Oblivion folder in My Games (after backing up the save games you want to keep), and all registry entries for Oblivion and, if applicable, mods and unofficial patches. Incomplete un-installations are among the main reasons why Oblivion refuses to start. If, after un-installing Oblivion, one of the two folders I mentioned, or Oblivion's registry entries are still there, your un-installation is incomplete, and any new installation is likely to fail when you try to start Oblivion.