diff --git a/bin/baseset/orig_win.obm b/bin/baseset/orig_win.obm
index 8e2053e..c8c4923 100644
--- a/bin/baseset/orig_win.obm
+++ b/bin/baseset/orig_win.obm
@@ -142,5 +142,17 @@ GM_TT19.GM = Funk Central
 GM_TT20.GM = Jammit
 GM_TT21.GM = Movin' On
 
+; MIDI timecodes where the playback should attemp to start and stop short.
+; This is to allow fixing undesired silences in original MIDI files.
+; However not all music drivers may support this.
+[timingtrim]
+; Theme has two beats silence at the beginning which prevents clean looping.
+GM_TT00.GM = 768:53760
+; Can't Get There From Here from the Windows version has a long silence at the end,
+; followed by a solo repeat. This isn't in the original DOS version music and is likely
+; unintentional from the people who converted the music from the DOS version.
+; Actual song ends after measure 152.
+GM_TT10.GM = 0:235008
+
 [origin]
 default      = You can find it on your Transport Tycoon Deluxe CD-ROM.
diff --git a/src/base_media_base.h b/src/base_media_base.h
index d5de6c3..43928dd 100644
--- a/src/base_media_base.h
+++ b/src/base_media_base.h
@@ -286,6 +286,9 @@ struct MusicSet : BaseSet<MusicSet, NUM_SONGS_AVAILABLE, false> {
 	char song_name[NUM_SONGS_AVAILABLE][32];
 	byte track_nr[NUM_SONGS_AVAILABLE];
 	byte num_available;
+	int override_start[NUM_SONGS_AVAILABLE];
+	int override_end[NUM_SONGS_AVAILABLE];
+	bool has_theme;
 
 	bool FillSetDetails(struct IniFile *ini, const char *path, const char *full_filename);
 };
diff --git a/src/music.cpp b/src/music.cpp
index 4001e62..4511ce6 100644
--- a/src/music.cpp
+++ b/src/music.cpp
@@ -65,8 +65,13 @@ bool MusicSet::FillSetDetails(IniFile *ini, const char *path, const char *full_f
 	bool ret = this->BaseSet<MusicSet, NUM_SONGS_AVAILABLE, false>::FillSetDetails(ini, path, full_filename);
 	if (ret) {
 		this->num_available = 0;
+		this->has_theme = !StrEmpty(this->files[0].filename);
+		
+		uint next_track_nr = 1;
+
 		IniGroup *names = ini->GetGroup("names");
-		for (uint i = 0, j = 1; i < lengthof(this->song_name); i++) {
+		IniGroup *timingtrim = ini->GetGroup("timingtrim");
+		for (uint i = 0; i < lengthof(this->song_name); i++) {
 			const char *filename = this->files[i].filename;
 			if (names == NULL || StrEmpty(filename)) {
 				this->song_name[i][0] = '\0';
@@ -74,15 +79,16 @@ bool MusicSet::FillSetDetails(IniFile *ini, const char *path, const char *full_f
 			}
 
 			IniItem *item = NULL;
+			const char *trimmed_filename = filename;
 			/* As we possibly add a path to the filename and we compare
 			 * on the filename with the path as in the .obm, we need to
 			 * keep stripping path elements until we find a match. */
-			for (const char *p = filename; p != NULL; p = strchr(p, PATHSEPCHAR)) {
+			for (; trimmed_filename != NULL; trimmed_filename = strchr(trimmed_filename, PATHSEPCHAR)) {
 				/* Remove possible double path separator characters from
 				 * the beginning, so we don't start reading e.g. root. */
-				while (*p == PATHSEPCHAR) p++;
+				while (*trimmed_filename == PATHSEPCHAR) trimmed_filename++;
 
-				item = names->GetItem(p, false);
+				item = names->GetItem(trimmed_filename, false);
 				if (item != NULL && !StrEmpty(item->value)) break;
 			}
 
@@ -92,8 +98,18 @@ bool MusicSet::FillSetDetails(IniFile *ini, const char *path, const char *full_f
 			}
 
 			strecpy(this->song_name[i], item->value, lastof(this->song_name[i]));
-			this->track_nr[i] = j++;
 			this->num_available++;
+			/* if there is a theme song, number that one zero */
+			this->track_nr[i] = (i==0 && this->has_theme) ? 0 : next_track_nr++;
+
+			item = timingtrim->GetItem(trimmed_filename, false);
+			if (item != NULL && !StrEmpty(item->value)) {
+				const char *endpos = strchr(item->value, ':');
+				if (endpos != NULL) {
+					this->override_start[i] = atoi(item->value);
+					this->override_end[i] = atoi(endpos + 1);
+				}
+			}
 		}
 	}
 	return ret;
diff --git a/src/music/allegro_m.cpp b/src/music/allegro_m.cpp
index 77b4881..d434304 100644
--- a/src/music/allegro_m.cpp
+++ b/src/music/allegro_m.cpp
@@ -58,7 +58,7 @@ void MusicDriver_Allegro::Stop()
 	if (--_allegro_instance_count == 0) allegro_exit();
 }
 
-void MusicDriver_Allegro::PlaySong(const char *filename)
+void MusicDriver_Allegro::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	if (_midi != NULL) destroy_midi(_midi);
 	_midi = load_midi(filename);
diff --git a/src/music/allegro_m.h b/src/music/allegro_m.h
index 69cf595..68cac0d 100644
--- a/src/music/allegro_m.h
+++ b/src/music/allegro_m.h
@@ -21,7 +21,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/bemidi.cpp b/src/music/bemidi.cpp
index 2bc2074..a34e5a1 100644
--- a/src/music/bemidi.cpp
+++ b/src/music/bemidi.cpp
@@ -34,7 +34,7 @@ void MusicDriver_BeMidi::Stop()
 	midiSynthFile.UnloadFile();
 }
 
-void MusicDriver_BeMidi::PlaySong(const char *filename)
+void MusicDriver_BeMidi::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	this->Stop();
 	entry_ref midiRef;
diff --git a/src/music/bemidi.h b/src/music/bemidi.h
index 23c6249..fb8ce1c 100644
--- a/src/music/bemidi.h
+++ b/src/music/bemidi.h
@@ -21,7 +21,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/cocoa_m.cpp b/src/music/cocoa_m.cpp
index 925dc21..b68ee6e 100644
--- a/src/music/cocoa_m.cpp
+++ b/src/music/cocoa_m.cpp
@@ -143,7 +143,7 @@ void MusicDriver_Cocoa::Stop()
  *
  * @param filename Path to a MIDI file.
  */
-void MusicDriver_Cocoa::PlaySong(const char *filename)
+void MusicDriver_Cocoa::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	DEBUG(driver, 2, "cocoa_m: trying to play '%s'", filename);
 
diff --git a/src/music/cocoa_m.h b/src/music/cocoa_m.h
index 1963bef..cc9d453 100644
--- a/src/music/cocoa_m.h
+++ b/src/music/cocoa_m.h
@@ -20,7 +20,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/dmusic.cpp b/src/music/dmusic.cpp
index 94f556e..4d366ef 100644
--- a/src/music/dmusic.cpp
+++ b/src/music/dmusic.cpp
@@ -221,7 +221,7 @@ void MusicDriver_DMusic::Stop()
 }
 
 
-void MusicDriver_DMusic::PlaySong(const char *filename)
+void MusicDriver_DMusic::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	/* set up the loader object info */
 	DMUS_OBJECTDESC obj_desc;
@@ -257,6 +257,19 @@ void MusicDriver_DMusic::PlaySong(const char *filename)
 		return;
 	}
 
+	/* All original TTD music has a timedivision of 384, while DirectMusic internally
+	 * works with a timedivision of 768 i.e. double. Not hardcoding this would require
+	 * either more addendum data in the baseset files, or reading a couple bytes from
+	 * the MIDI files to get the actual timedivision, and scale accordingly. */
+	time_start *= 2;
+	time_end *= 2;
+	segment->SetStartPoint(time_start);
+	/* Enable looping if required */
+	if (time_end > time_start && loop) {
+		segment->SetLoopPoints(time_start, time_end);
+		segment->SetRepeats(DMUS_SEG_REPEAT_INFINITE);
+	}
+
 	/* tell the segment to 'download' the instruments */
 	if (FAILED(segment->SetParam(GUID_Download, 0xFFFFFFFF, 0, 0, performance))) {
 		DEBUG(driver, 0, "DirectMusic: failed to download instruments");
@@ -264,11 +277,18 @@ void MusicDriver_DMusic::PlaySong(const char *filename)
 	}
 
 	/* start playing the MIDI file */
+	MUSIC_TIME perf_time_start = 0;
+	performance->GetTime(NULL, &perf_time_start);
 	if (FAILED(performance->PlaySegment(segment, 0, 0, NULL))) {
 		DEBUG(driver, 0, "DirectMusic: PlaySegment failed");
 		return;
 	}
 
+	/* If an ending time is given, request a stop at that point */
+	if (time_end > time_start && !loop) {
+		performance->Stop(segment, NULL, perf_time_start + time_end, DMUS_SEGF_DEFAULT);
+	}
+
 	seeking = true;
 }
 
diff --git a/src/music/dmusic.h b/src/music/dmusic.h
index 7287623..8a31eb5 100644
--- a/src/music/dmusic.h
+++ b/src/music/dmusic.h
@@ -23,7 +23,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/extmidi.cpp b/src/music/extmidi.cpp
index d39a050..572e11a 100644
--- a/src/music/extmidi.cpp
+++ b/src/music/extmidi.cpp
@@ -83,7 +83,7 @@ void MusicDriver_ExtMidi::Stop()
 	this->DoStop();
 }
 
-void MusicDriver_ExtMidi::PlaySong(const char *filename)
+void MusicDriver_ExtMidi::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	strecpy(this->song, filename, lastof(this->song));
 	this->DoStop();
diff --git a/src/music/extmidi.h b/src/music/extmidi.h
index cfbd894..5724b34 100644
--- a/src/music/extmidi.h
+++ b/src/music/extmidi.h
@@ -28,7 +28,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/libtimidity.cpp b/src/music/libtimidity.cpp
index 1cb2adc..a50991e 100644
--- a/src/music/libtimidity.cpp
+++ b/src/music/libtimidity.cpp
@@ -96,7 +96,7 @@ void MusicDriver_LibTimidity::Stop()
 	mid_exit();
 }
 
-void MusicDriver_LibTimidity::PlaySong(const char *filename)
+void MusicDriver_LibTimidity::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	this->StopSong();
 
diff --git a/src/music/libtimidity.h b/src/music/libtimidity.h
index abe17e7..2ee7ecc 100644
--- a/src/music/libtimidity.h
+++ b/src/music/libtimidity.h
@@ -21,7 +21,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/music_driver.hpp b/src/music/music_driver.hpp
index be09d3e..5a0d5f5 100644
--- a/src/music/music_driver.hpp
+++ b/src/music/music_driver.hpp
@@ -21,7 +21,7 @@ public:
 	 * Play a particular song.
 	 * @param filename The name of file with the song to play.
 	 */
-	virtual void PlaySong(const char *filename) = 0;
+	virtual void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false) = 0;
 
 	/**
 	 * Stop playing the current song.
diff --git a/src/music/null_m.h b/src/music/null_m.h
index df9f7d8..0e615bd 100644
--- a/src/music/null_m.h
+++ b/src/music/null_m.h
@@ -21,7 +21,7 @@ public:
 
 	/* virtual */ void Stop() { }
 
-	/* virtual */ void PlaySong(const char *filename) { }
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false) { }
 
 	/* virtual */ void StopSong() { }
 
diff --git a/src/music/os2_m.cpp b/src/music/os2_m.cpp
index d7fb97d..622008e 100644
--- a/src/music/os2_m.cpp
+++ b/src/music/os2_m.cpp
@@ -49,7 +49,7 @@ static long CDECL MidiSendCommand(const char *cmd, ...)
 /** OS/2's music player's factory. */
 static FMusicDriver_OS2 iFMusicDriver_OS2;
 
-void MusicDriver_OS2::PlaySong(const char *filename)
+void MusicDriver_OS2::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	MidiSendCommand("close all");
 
diff --git a/src/music/os2_m.h b/src/music/os2_m.h
index f35e2fd..f01b0bf 100644
--- a/src/music/os2_m.h
+++ b/src/music/os2_m.h
@@ -21,7 +21,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/qtmidi.cpp b/src/music/qtmidi.cpp
index 9bc6a61..4219695 100644
--- a/src/music/qtmidi.cpp
+++ b/src/music/qtmidi.cpp
@@ -258,7 +258,7 @@ void MusicDriver_QtMidi::Stop()
  *
  * @param filename Path to a MIDI file.
  */
-void MusicDriver_QtMidi::PlaySong(const char *filename)
+void MusicDriver_QtMidi::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	if (!_quicktime_started) return;
 
diff --git a/src/music/qtmidi.h b/src/music/qtmidi.h
index f0e1708..4b29324 100644
--- a/src/music/qtmidi.h
+++ b/src/music/qtmidi.h
@@ -20,7 +20,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music/win32_m.cpp b/src/music/win32_m.cpp
index fff0376..e1e7f07 100644
--- a/src/music/win32_m.cpp
+++ b/src/music/win32_m.cpp
@@ -31,7 +31,7 @@ static struct {
 
 static FMusicDriver_Win32 iFMusicDriver_Win32;
 
-void MusicDriver_Win32::PlaySong(const char *filename)
+void MusicDriver_Win32::PlaySong(const char *filename, int time_start, int time_end, bool loop)
 {
 	assert(filename != NULL);
 	strecpy(_midi.start_song, filename, lastof(_midi.start_song));
diff --git a/src/music/win32_m.h b/src/music/win32_m.h
index 3efee32..cec1b1c 100644
--- a/src/music/win32_m.h
+++ b/src/music/win32_m.h
@@ -21,7 +21,7 @@ public:
 
 	/* virtual */ void Stop();
 
-	/* virtual */ void PlaySong(const char *filename);
+	/* virtual */ void PlaySong(const char *filename, int time_start = 0, int time_end = 0, bool loop = false);
 
 	/* virtual */ void StopSong();
 
diff --git a/src/music_gui.cpp b/src/music_gui.cpp
index 279f376..3695203 100644
--- a/src/music_gui.cpp
+++ b/src/music_gui.cpp
@@ -109,6 +109,7 @@ void InitializeMusic()
 	uint j = 0;
 	for (uint i = 0; i < NUM_SONGS_AVAILABLE; i++) {
 		if (StrEmpty(GetSongName(i))) continue;
+		if (i == 0 && BaseMusic::GetUsedSet()->has_theme) continue;
 		_playlist_all[j++] = i + 1;
 	}
 	/* Terminate the list */
@@ -182,10 +183,16 @@ static void MusicVolumeChanged(byte new_vol)
 static void DoPlaySong()
 {
 	char filename[MAX_PATH];
-	if (FioFindFullPath(filename, lastof(filename), BASESET_DIR, BaseMusic::GetUsedSet()->files[_music_wnd_cursong - 1].filename) == NULL) {
-		FioFindFullPath(filename, lastof(filename), OLD_GM_DIR, BaseMusic::GetUsedSet()->files[_music_wnd_cursong - 1].filename);
+	int songid = _music_wnd_cursong - 1;
+	const MusicSet &set = *BaseMusic::GetUsedSet();
+	if (FioFindFullPath(filename, lastof(filename), BASESET_DIR, set.files[songid].filename) == NULL) {
+		FioFindFullPath(filename, lastof(filename), OLD_GM_DIR, set.files[songid].filename);
 	}
-	MusicDriver::GetInstance()->PlaySong(filename);
+	bool loop = false;
+	if (_music_wnd_cursong == 1 && _game_mode == GM_MENU && set.has_theme) {
+		loop = true;
+	}
+	MusicDriver::GetInstance()->PlaySong(filename, set.override_start[songid], set.override_end[songid], loop);
 	SetWindowDirty(WC_MUSIC_WINDOW, 0);
 }
 
@@ -243,6 +250,16 @@ static void StopMusic()
 
 static void PlayPlaylistSong()
 {
+	if (_game_mode == GM_MENU && BaseMusic::GetUsedSet()->has_theme) {
+		/* force first song (theme) on the main menu.
+		 * this is guaranteed to exist, otherwise
+		 * has_theme would not be set. */
+		_music_wnd_cursong = 1;
+		DoPlaySong();
+		_song_is_active = true;
+		return;
+	}
+
 	if (_cur_playlist[0] == 0) {
 		SelectSongToPlay();
 		/* if there is not songs in the playlist, it may indicate
@@ -268,8 +285,19 @@ void ResetMusic()
 	DoPlaySong();
 }
 
+/**
+ * Check music playback status and start/stop/song-finished
+ * Called from main loop.
+ */
 void MusicLoop()
 {
+	static GameMode _last_game_mode = GM_BOOTSTRAP;
+	bool force_restart = false;
+	if (_game_mode != _last_game_mode) {
+		force_restart = true;
+		_last_game_mode = _game_mode;
+	}
+
 	if (!_settings_client.music.playing && _song_is_active) {
 		StopMusic();
 	} else if (_settings_client.music.playing && !_song_is_active) {
@@ -278,13 +306,13 @@ void MusicLoop()
 
 	if (!_song_is_active) return;
 
-	if (!MusicDriver::GetInstance()->IsSongPlaying()) {
-		if (_game_mode != GM_MENU) {
+	if (force_restart || !MusicDriver::GetInstance()->IsSongPlaying()) {
+		if (_game_mode == GM_MENU && BaseMusic::GetUsedSet()->has_theme) {
+			ResetMusic();
+		} else {
 			StopMusic();
 			SkipToNextSong();
 			PlayPlaylistSong();
-		} else {
-			ResetMusic();
 		}
 	}
 }