It works

Fonts are hinted pretty well at this size, looks sharp.

appinfo.json

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+{
+    "appKeys": {},
+    "capabilities": [
+        ""
+    ],
+    "companyName": "dartcatcher@gmail.com",
+    "longName": "Helvetica",
+    "projectType": "native",
+    "resources": {
+        "media": [
+            {
+                "characterRegex": "[0-9A-Za-z ]",
+                "file": "fonts/helveticaneue.ttf",
+                "name": "HELVETICA_R_28",
+                "type": "font"
+            },
+            {
+                "characterRegex": "[0-9:]",
+                "file": "fonts/HelveticaNeue-Bold.ttf",
+                "name": "HELVETICA_B_48",
+                "type": "font"
+            }
+        ]
+    },
+    "sdkVersion": "2",
+    "shortName": "Helvetica",
+    "uuid": "534e5853-7be7-447e-a67d-b236ac9f4f51",
+    "versionCode": 1,
+    "versionLabel": "1.0",
+    "watchapp": {
+        "watchface": true
+    }
+}

src/main.c

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+#include "pebble.h"
+
+static Window *s_main_window;
+static TextLayer *s_date_layer, *s_time_layer;
+static Layer *s_line_layer;
+
+static void line_layer_update_callback(Layer *layer, GContext* ctx) {
+  graphics_context_set_fill_color(ctx, GColorWhite);
+  graphics_fill_rect(ctx, layer_get_bounds(layer), 0, GCornerNone);
+}
+
+static void handle_minute_tick(struct tm *tick_time, TimeUnits units_changed) {
+  // Need to be static because they're used by the system later.
+  static char s_time_text[] = "00:00";
+  static char s_date_text[] = "Xxxxxxxxx 00";
+
+  strftime(s_date_text, sizeof(s_date_text), "%e %b", tick_time);
+  text_layer_set_text(s_date_layer, s_date_text);
+
+  char *time_format;
+  if (clock_is_24h_style()) {
+    time_format = "%R";
+  } else {
+    time_format = "%I:%M";
+  }
+  strftime(s_time_text, sizeof(s_time_text), time_format, tick_time);
+
+  // Handle lack of non-padded hour format string for twelve hour clock.
+  if (!clock_is_24h_style() && (s_time_text[0] == '0')) {
+    memmove(s_time_text, &s_time_text[1], sizeof(s_time_text) - 1);
+  }
+  text_layer_set_text(s_time_layer, s_time_text);
+}
+
+static void main_window_load(Window *window) {
+  Layer *window_layer = window_get_root_layer(window);
+
+  s_date_layer = text_layer_create(GRect(8, 66, 136, 100));
+  text_layer_set_text_color(s_date_layer, GColorWhite);
+  text_layer_set_background_color(s_date_layer, GColorClear);
+  text_layer_set_font(s_date_layer, fonts_load_custom_font(resource_get_handle(RESOURCE_ID_HELVETICA_R_28)));
+  layer_add_child(window_layer, text_layer_get_layer(s_date_layer));
+
+  s_time_layer = text_layer_create(GRect(7, 92, 137, 76));
+  text_layer_set_text_color(s_time_layer, GColorWhite);
+  text_layer_set_background_color(s_time_layer, GColorClear);
+  text_layer_set_font(s_time_layer, fonts_load_custom_font(resource_get_handle(RESOURCE_ID_HELVETICA_B_48)));
+  layer_add_child(window_layer, text_layer_get_layer(s_time_layer));
+}
+
+static void main_window_unload(Window *window) {
+  text_layer_destroy(s_date_layer);
+  text_layer_destroy(s_time_layer);
+
+  layer_destroy(s_line_layer);
+}
+
+static void init() {
+  s_main_window = window_create();
+  window_set_background_color(s_main_window, GColorBlack);
+  window_set_window_handlers(s_main_window, (WindowHandlers) {
+    .load = main_window_load,
+    .unload = main_window_unload,
+  });
+  window_stack_push(s_main_window, true);
+
+  tick_timer_service_subscribe(MINUTE_UNIT, handle_minute_tick);
+  
+  // Prevent starting blank
+  time_t now = time(NULL);
+  struct tm *t = localtime(&now);
+  handle_minute_tick(t, MINUTE_UNIT);
+}
+
+static void deinit() {
+  window_destroy(s_main_window);
+
+  tick_timer_service_unsubscribe();
+}
+
+int main() {
+  init();
+  app_event_loop();
+  deinit();
+}

wscript

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+
+#
+# This file is the default set of rules to compile a Pebble project.
+#
+# Feel free to customize this to your needs.
+#
+
+import os.path
+try:
+    from sh import CommandNotFound, jshint, cat, ErrorReturnCode_2
+    hint = jshint
+except (ImportError, CommandNotFound):
+    hint = None
+
+top = '.'
+out = 'build'
+
+def options(ctx):
+    ctx.load('pebble_sdk')
+
+def configure(ctx):
+    ctx.load('pebble_sdk')
+    global hint
+    if hint is not None:
+        hint = hint.bake(['--config', 'pebble-jshintrc'])
+
+def build(ctx):
+    if False and hint is not None:
+        try:
+            hint([node.abspath() for node in ctx.path.ant_glob("src/**/*.js")], _tty_out=False) # no tty because there are none in the cloudpebble sandbox.
+        except ErrorReturnCode_2 as e:
+            ctx.fatal("\nJavaScript linting failed (you can disable this in Project Settings):\n" + e.stdout)
+
+    # Concatenate all our JS files (but not recursively), and only if any JS exists in the first place.
+    ctx.path.make_node('src/js/').mkdir()
+    js_paths = ctx.path.ant_glob(['src/*.js', 'src/**/*.js'])
+    if js_paths:
+        ctx(rule='cat ${SRC} > ${TGT}', source=js_paths, target='pebble-js-app.js')
+        has_js = True
+    else:
+        has_js = False
+
+    ctx.load('pebble_sdk')
+
+    ctx.pbl_program(source=ctx.path.ant_glob('src/**/*.c'),
+                    target='pebble-app.elf')
+
+    if os.path.exists('worker_src'):
+        ctx.pbl_worker(source=ctx.path.ant_glob('worker_src/**/*.c'),
+                        target='pebble-worker.elf')
+        ctx.pbl_bundle(elf='pebble-app.elf',
+                        worker_elf='pebble-worker.elf',
+                        js='pebble-js-app.js' if has_js else [])
+    else:
+        ctx.pbl_bundle(elf='pebble-app.elf',
+                       js='pebble-js-app.js' if has_js else [])
+